We know that finding the right audience and then giving them compelling reasons to continue to support your work is core to being successful on Substack. The features we launched this month allow you to do both these things: reach new subscribers and create richer experiences for your existing ones. Here’s the latest.

Creator match

Starting today, all publishers have access to creator match, a new feature that helps you easily find relevant collaborations with other publishers. Creator match identifies writers and creators with similar audience sizes and interests, then curates them for you, ranked by how promising the collaboration could be for both of you. You can find the feature in your publisher dashboard.

Collaborating with other Substack publishers is one of the most powerful routes to grow on the platform, and it’s how many Bestsellers got their start. of Lenny’s Newsletter and of Elena’s Growth Scoop; of Not Boring and of Noahpinion have collaborated via cross-posts, recommendations, and podcast episodes, or shared each other’s work in a Note. These collaborations put your work in front of like-minded audiences and give new readers a reason to subscribe: they’re discovering you via a publisher they already trust.

You can message fellow publishers directly from the creator match dashboard to initiate a collaboration.

Segments and tags

Instead of seeing your audience as one big subscriber list, you can now use segments and tags to connect with specific groups directly. Target a post to a segment, such as readers in Alaska, or tag people who attended your last event, and give them more of what they like about your work.

, publisher of the saturday essay, assigns tags to new subscribers as they come in. He then uses those tags to create segments and send posts selectively to those audience subgroups.

Learn more about segments and tags in our Help Center.

Audience-specific content blocks

You can now tailor sections of a post for different groups without creating separate posts for each one. You can add personalized content blocks to written, podcast, or video posts that are visible based on a reader’s subscription status, including free, paid, or founding subscribers.

uses audience-specific content blocks to tailor calls to action based on who’s reading.

Learn more about audience-specific content in our Help Center.

Reply rules are available to non-English publications

In June, we launched reply rules to help you shape the conversation happening across your Substack community. This feature allows you to set your own community standards and auto-hide post comments, note replies, and subscriber chats that don’t meet them. The system learns every time you hide a reply and preemptively moderates replies it thinks you would take action on yourself.

Now reply rules are available to non-English publications and apply to non-English comments and replies, so everyone can set the terms for their corner of the internet, no matter where they live or what language they speak.

Learn more about reply rules in our Help Center.

Subscriber-only comments

Different posts can elicit different kinds of conversation. You can now choose who gets to comment on each post, giving you more control over who participates. Set your comment section to include:

• Everyone (subscribers and non-subscribers)

• Free and paid subscribers

• Paid subscribers only

• No one

, the publisher of Bar Harbor Story, a local media outlet serving the Mount Desert Island region of Maine and Acadia National Park, opens comments to free and paid subscribers.

Carrie says, “Because we’re a community next to a national park, we have some hot-button issues. Having subscriber-only comments helps us cut down on bots and make community members feel safer when they comment. It becomes more like a playground with rules in the comment section, rather than a no-holds-barred WWF sort of showdown.”

Learn more about subscriber-only comments in our Help Center.

Podcast transcript advanced editing features

We’ve improved our transcript editing tools to make multi-speaker episodes easier to edit. You can now:

• Merge speakers when our transcript generator identifies more speakers than your podcast has

• Label unassigned speakers, reassign speakers, and correct labeling errors

, the co-host of Split Zone Duo, knows the pain of bad transcripts and how much time a tool like this can save a podcast creator who’s on a tight timeline covering college football: “Bad transcripts are gibberish, and a script that doesn’t understand proper nouns is useless. Every step toward a transcript that’s low-effort and high-trust is a step toward a less frustrating world. I’d much rather read my own words back to myself than endure the nails-on-chalkboard experience of listening back to specific sections or (heaven forbid) an entire show just to find something.”

Learn more about advanced podcast editing in our Help Center.

Typefully partnership

Substack is now integrated with Typefully, a platform used by creators to schedule and publish content across multiple platforms—like X, Threads, LinkedIn, and Bluesky—from one place. If you write a Note or post on X sharing your most recent work, you can increase discoverability where people already follow you. This also gives your audience a path back to your Substack.

If you have a story about how a specific feature or best practice helped you grow your Substack, let us know in a Note, in a post, or by restacking. Thanks for being here.

Earlier this year, veteran national security reporter was served with an eye-watering $1 million defamation lawsuit after publishing a scoop about an incoming Trump administration official in his publication, SpyTalk. Backed by a number of authoritative sources, Jeff had reported that Keith Bass, the Pentagon’s incoming top health official, had been “effectively fired” from his previous role at the CIA for “poor management”. He turned to Substack Defender, which offers Substack publishers legal support as part of efforts to uphold a free press and free speech, to fight the case. With Defender’s support, the case was dismissed with prejudice last week in federal court.

SpyTalk has been on Substack since 2020, when Jeff brought his longtime column, previously at Newsweek and the Washington Post, to the platform and expanded it into a ring of seasoned reporters and experts breaking news and offering analysis on the world of clandestine operations. He also knows that world from the inside: before becoming a journalist, he served as a U.S. Army intelligence case officer in Vietnam. We spoke with him about threats to journalism, his experience with the lawsuit, and what it’s like to cover power and secrecy over a decades-long career.

You’ve written that legal threats like this are mostly nuisance suits but they still “suck up your time, your mind space, and your sleep.” What was it like to be served?

Well, at first it was a bit of a shock that I was being sued by this guy, and then as I read through the summons, I just scoffed, and I thought, this guy doesn’t have a case whatsoever. I was very confident about my facts, this piece had been thoroughly researched by myself, and my sources were authoritative. I couldn’t understand why he filed the suit, really.

[Without Defender] I would have had to go out searching on my own for somebody who might take on the case pro bono. The initial cost of just responding is really expensive. I’m not going to name how much [the lawyers] billed Substack, but it was in the tens of thousands of dollars just for these motions. We made a motion, they responded, we made another motion, then we had to go to court—and this is the baby steps of the legal dispute, right, just the initial steps, so you can imagine how much [a long-term case] costs. I look at my assets, which are pretty typical for a journalist, which is not a lot. My main asset being my house, I would have to sell it and, I don’t know, move into a one-room apartment? Something like that. These are the things that make you toss and turn at night.

Was this your first time getting help from the Defender program?

Three or four years ago I had a story that I thought might generate a defamation suit, so I wanted to run some paragraphs by the Defender lawyers, and they were great. They very quickly reviewed the copy and made a suggestion or two of rewording, which I did.

What happened this time around, when you applied for legal support for the Bass lawsuit?

I was very confident about it, because it was a clear First Amendment case—the guy was trying to shut down a journalist for reporting the truth. I wrote to the generic address for the Defender program, and I got a response within two days. I got a call, and they said: we think this is a case that we can get behind, so we’re reaching out to a law firm in Virginia and they’ll take on your case pro bono. That was all music to my ears. Then those lawyers, who turned out to be two terrific women, really brilliant lawyers in Arlington, in a firm right across the river from me in Washington, reached out to me, and we got on the phone and talked. They were terrific from the beginning—they said all the right things a lawyer should say. They said, calm down, don’t worry, we’ve got it, we don’t think there’s much merit to this suit, and with your permission we will go to court and fight for you. And off we went.

Did you work closely with the attorneys as they went to court?

I’m the client, so they have to discuss every move they make with me. They wrote, “Here’s the draft of our response to the summons,” for example—a 20-page, very erudite, tightly argued [filing], asking the court to dismiss the case because there was no real basis for it, either by the facts of the piece or by existing law, and that it should qualify as one of the so-called SLAPP cases—which stands for “strategic [lawsuit] against public participation,” but I like to say “silly litigation against reporters.” Anyway, it was great, the lawyers were great, and we won. Happy ending.

How have you built SpyTalk into a multi-channel news operation, with several top reporters and experts writing alongside you?

I first started SpyTalk as a column when I was at Congressional Quarterly, almost 20 years ago. It began as a weekly column, then became a daily column, and, as the title suggests, I covered national security topics with particular interest in intelligence operations—operations at the CIA, NSA, FBI, relevant departments of the Justice Department, etc. After I left CQ, I went to the Washington Post and did SpyTalk there for a couple years, and then I went to Newsweek for six, seven years, and then that was another corporate restructuring and a bunch of us were laid off. So I was really open to any possibilities. I wasn’t ready to hang up my spurs yet.

I freelanced a little for a while, and then I noticed a friend of mine who’s a China specialist, , had moved from Slate to this thing called Substack, so I called him up and said, “What’s that all about?” He said it’s great, he said he wasn’t getting any satisfaction from Slate, and he knew these guys at Substack and they invited him over. He said, “I do what I’ve always done, but I have a direct relationship with readers, and I’m making more money than Slate could ever pay me. I’m making six figures, and I’ve only done it for six months. I said, “Fabulous. I said, “Do you think they’d be interested in SpyTalk?” and he said, “Of course they would.”

I got to talking about this with a bunch of longtime journalist friends who are very accomplished, from the Washington Post, wire services, Newsweek, Time magazine, and so on. So we decided to sort of do SpyTalk as a group, and we got it off the ground. We published our first story on August 31st, 2020. It’s six years ago this month, and we’re having a big party in September to mark the anniversary, at a local pub in D.C. It’s been terrific, and we had really stellar contributors right from the beginning, people who had held senior editorial positions at other legacy media publications who were, like me, sort of long in the tooth but not ready to hang it up. The burden would be particularly on me, but right from the beginning I had these other contributors who’ve changed over time but are still important cogs in the SpyTalk machinery. We launched a podcast about two years in as well, and that’s going well too.

Congratulations on six years! What do you consider your breakthrough stories?

One of the writers who came on in recent years is , very well-known investigative reporter, formerly Washington Post, Newsweek, NBC News, etc. He came with a following, but he’s a scoop artist, so when he has a scoop, we get a lot [of engagement]—I mean, we’re not reinventing the wheel here. Scoops draw readers for sure, but readers also like thoughtful pieces. We do a fair amount of book reviewing, books that deal with espionage, the spy world, and even movies and TV, and that draws subscribers in. I find that, generally speaking, you get lots of responses to scoops, but I really think it’s the thoughtful stuff that generates subscribers who stick with us. I think they’re looking for serious journalism, and we get high marks for taking on serious topics, bringing a fresh eye to ongoing scandals and crises, like the Iran war, for example.

Legacy outlets often have institutional caution baked in—lawyers reviewing copy, editors weighing the risks of publishing something. I’m curious how it feels to work without that support and if it’s changed what you’re willing to publish now that you’re working independently?

I’m the quote-unquote “boss,” but I’m really just the ringmaster of the circus. We’re all deeply experienced—I’ve been covering this stuff for 40-plus years, and others on the team have been covering it for 20-plus or more, like me, 40 years or more. So we know how we should say things carefully, we know what the rules of the road are in terms of our coverage. The suit against me by this Trump administration official, former head of the CIA’s medical office, was generated because I used “fired” in a headline and “effectively fired” in the lede, and he took great umbrage. But I have multiple sources telling me he was forced out of the CIA, as I reported in my piece, so there was no doubt about the accuracy of it. I’ve only been threatened with one suit since I started SpyTalk on Substack, only once, and that was just a letter from a lawyer saying we see grounds for pursuing you, and that was in regard to Tulsi Gabbard and the cult she’s been tied up with in Hawaii. The cult group, their lawyers, wrote me a stiff letter, and I said, “Point out the areas where I’ve gotten anything wrong and I’ll deal with it.” I never heard from them again. I can’t remember any other time in my 40-year career that I’ve been even threatened with a libel suit.

What would be different if you were still working at a place like the Washington Post?

I’d have to send my shirts and jackets to the dry cleaner. I had to have better clothes, pants, good shoes. A tie has gone the way of the dinosaur, generally speaking.

How has SpyTalk grown over the years?

It’s been growing year after year since we launched. It was kind of a shock, actually, when we put out the first story, and within a couple days there were like a thousand subscribers, and I thought, people are paying for this, now I’ve got to do another story, and another, and another, forever. I’ve got to keep it going. A lot of that was because I had developed a following in my niche-within-a-niche over the years, plus my other collaborators had followers too. We’ve grown, I would say, on average, 5% to 10% every year.

And you can pay your contributors at a rate that rivals the New York Times op-ed rate!

I used to write op-eds for the New York Times and book reviews, and I was paid anywhere from, I think, $600 to $750, something like that. Freelance rates, as you may know, have collapsed over the last 20 years. The last slick magazine piece I did was for GQ magazine in 2000, I got paid $20,000 for it, and those [outlets] just aren’t paying like that anymore, thanks to the internet, and thanks in particular to Huffington Post, which invited people to write for free—horrible idea. I dip into discussions every once in a while where people say, “I’ve been writing for six months and I’ve only got 30 followers” or whatever. Well, it depends what you’re writing, people do respond to quality and timeliness and insight. That’s been gratifying to discover, that people want quality journalism, so I think if you produce that, you’ve got a good chance to thrive on Substack.

Interview was edited for length and clarity.

We want to have an honest conversation about how publishers are feeling about and using AI. These tools are in their infancy, and while the norms around their use and disclosure are evolving rapidly, we think it’s important to ask top writers, creators, and thinkers about their work, their businesses, and how they intersect with where AI stands today.

That’s why we’re introducing Model Behavior, a new series featuring public intellectuals, critics, writers, and creators discussing how they work in this moment. We’ll ask candid questions about the tech industry, AI pet peeves, how it’s impacting their sense of identity and livelihoods. We’ll also ask each guest to give us a behind-the-scenes look at their creative process and explain whether and how they use these tools. From anti-AI purists to power users, we’ll get into the prompts they choose, their tool stacks, or their 100% analog workflows.

We start off this week with , the founder of User Mag.

Do you find yourself altering your writing style to sound “less AI”?

Oh my gosh. A while ago, I wrote a piece for Vanity Fair where I used the phrase “deeply human.” That’s actually a phrase I use a lot. I use adverbs a lot. And somebody was like, “This is AI.” I actually had to show the edit history to prove it was my own bad writing.

How much do you spend on AI tools every month?

Probably about $300 a month.

When does AI use cross over from “tool” into “something I’d owe my readers a disclosure about”?

I think the more transparency the better, and I believe in answering readers’ questions and being open. I’m doing this interview because I happily talk about how I use these tools. When you don’t give readers the information, you’re not allowing them to evaluate the information they’re consuming in context. A lot of writers use AI, and they don’t want to talk about it because they think they’ll be canceled or get all this backlash, and people will hate them and unsubscribe. There is a lot of anti-AI sentiment, but I think part of getting through this phase we’re in is being transparent and open and having these conversations in the open and discussing this stuff publicly.

Would you read a newsletter where the copy was 100% AI-generated?

Absolutely, I love several newsletters that are AI-generated. I subscribe to a newsletter from a social listening tool that sends a weekly automated roundup of trending content and analysis of that content. It’s completely AI-generated, and I find it incredibly useful. There are newsletter writers I specifically follow for their taste and their voice or their unique writing. And then there are newsletters I get that I think are potentially automated or openly automated, or partially automated, I guess I should say, and I find a lot of value from those as well.

What are your AI pet peeves? Is there anything that irks you about how you see your peers using AI?

I’m in a lot of journalist groups. Journalists are using AI constantly. I think there are a lot of people who are very performative about AI online. They’ll spend all day shitting on AI 24/7, and then they’ll come into the group chat saying, “By the way, does anyone know how to use this new Claude tool?” I think that’s a disservice to readers, especially if you’re a tech writer. I am so critical of mass surveillance, I write critically about these AI companies, I write critically about their lobbying efforts, I report very critically on the AI industry, but I also cover consumer products, and I want people to understand how these products work. I don’t want to scare people with hyperbolic claims or misinformation, or just do things I know would get me more engagement.

If I got online every single day and ranted about how evil the AI industry is, or ranted about how AI is fake, it’s a bubble, nobody really uses it for anything, it’s all coming crashing down, and I’m not kidding—there are people who do that who are millionaires. Adding nuance to these conversations is not profitable. But I think it’s important.

Has AI changed how secure you feel in your own value as a writer?

I’m actually a terrible writer. I think I’ve gotten better, but I was a terrible writer when I started out. A really famous New York Times editor told me: if you want to be a journalist, the point is to expose new information. What LLMs cannot do—yet—is uncover things the way actual journalists can. AI has caused a great deal of instability in my career. I certainly question my ability to maintain a living as a journalist. I’ve been asking readers when they cancel to tell me why, and a lot of them are canceling because they just use AI to get their information now instead. That’s been quite devastating; I would say I’ve lost about a quarter of my income.

Have you changed your editorial strategy to counter that?

I am in the process of trying to figure that out. The way I’ve tried to adapt so far is to try to leverage these tools to be more productive. But I don’t know how to counter it, if at the current rate this continues, I will have lost half my income by the end of this year. Which is scary, and that’s not an indictment on any one platform like Substack; it’s a complete transformation in how people get information, and I think tech reporters, especially people who cover online culture, are seeing a lot of this. Because most of my newsletter was recommendations, that’s something AI can do better than me. It can scour the internet and find a story better than [I can]. The reason I don’t use AI for that portion is because I try to communicate to people, you are paying for access to my brain, for the news that I personally think is interesting. But I don’t think people care that much, and I think if they can get something even more tailored to their interests instead of mine, they’ll do it. So I’ve tried to do more original writing and communicate to my audience, “If you want me to remain an independent journalist and produce this content, please support me, because the news outlets I write for don’t pay anything.”

Every single big investigation I have done, I have lost thousands of dollars. It sounds so bleak, but at the same time, I love technology. I want a better world through technology; I support people getting their information from AI. I think we as a culture just need to recognize that it’s disrupting our information ecosystem, and think about what business models we can build to support journalism. Right now a lot of journalists are not going to be able to remain journalists. I’m also pivoting the coverage of my content because I was covering a lot of politics, which was bad for advertisers, so now I’m trying to cover more basic tech stuff because that’s more monetizable. I don’t personally mind that very much, but I’m not going to be exposing as much wrongdoing in the political ecosystem, and I’m not the only one making that decision.

Do you think the way the tech industry has rolled out AI has helped or hindered its adoption?

It’s a little bit of both. Let’s consider the fact that ChatGPT is the fastest-growing consumer product of all time, ever. Now that growth has slowed, of course, but there is enormous interest in this technology. Look at Anthropic, mostly a B2B business model but they have a huge consumer business. There are millions of people getting utility from AI products; you cannot ignore that. Look at the reviews on ChatGPT alone, they have over 6 million reviews in the iPhone store. I think they have like a 4.8 rating. People love these tools; people use them every single day to improve their lives.

At the same time, the people who run these tech companies are self-interested. They’re often bad actors. I disagree with their ideology. They will do anything to make money at all costs; they don’t always have the users in mind. I think they’ve failed to communicate the benefits of the technology to a lot of skeptics. People need to remember that AI is not just OpenAI and Anthropic, that large language models are a new technology, and personally, I use DeepSeek probably more than I use those other tools. So that’s another issue a lot of these people have—they think AI, they think Sam Altman.

What responsibility do platforms and AI companies have to writers and creators?

I think platforms should do everything they can to support creators. There are platforms that are predatory, like Meta, that absolutely do not materially support creators. X is not a platform that has supported creators; hopefully they start. And then there are platforms, I would argue like Substack or even YouTube, that offer scalable revenue generation. Substack is part of my income, enough to live on.

I also think how we should fund journalism is an open question, and I don’t think it should be on the tech companies necessarily to fix—their job is to build these products, not save journalism. But look at someone like Craig Newmark. Craigslist decimated the local news industry in a lot of ways, and he’s funded enormous journalism projects and saved so many outlets from peril. So I think these tech billionaires should consider their impact on the world, and if they can blunt that impact with their billions, consider doing that. So far, none of them have; I hope that changes.

Any advice for someone who wants to start in journalism in the midst of all of this?

I would tell them that the business model for journalism is in flux right now, so if you want to be a journalist, number one, build a direct relationship with an audience. That’s the most valuable thing you can do. And don’t shy away from new technology. The one advantage you have when you’re starting out is that you’re starting from scratch, so you can build your business model however you want. There are a lot of young people I talk to today who know journalism is going to be a hobby for them. They’ll become an HVAC technician and do journalism on the side, or make some other product and use that to fund their journalism. I don’t know that we’re going to have journalism the same way we had for the past 50 or 60 years. But we could build something better. We just have to have these conversations.

We asked Taylor Lorenz to take us through a day of research and writing, from a podcast episode to a newsletter, to give us some insight into her process and the decision points along the way.

PODCAST

My podcast, Power User, is a biweekly tech culture podcast, with special episodes on Fridays covering digital rights and free speech online called Free Speech Fridays.

RESEARCH

1. Aggregate research: when I’m getting up to speed on something I don’t know well, like security and LLMs for this week’s episode on the China open source model debate, I’ll take posts from someone I trust (in this instance ) and ask AI to pull together everything he’s said on the topic.

2. Search Gemini, and run queries on Grok to check for anything I missed.

3. Paste what I’ve gathered into Claude and ask it to organize the information.

4. Run similar searches across models to track the differences in their responses and understand each one’s capabilities better.

RECORD

1. Schedule a Riverside conversation with my guest for that week.

2. Record the conversation itself, human talking to human, no AI. I don’t write questions ahead of time; it makes the conversation feel less natural.

EDIT

1. Sometimes do a first cut myself in Adobe Premiere, sometimes send it straight to my human podcast editor.

2. My editor levels the audio, cuts any flubs, and puts together a draft of the episode, using AI tools in his process, especially for audio processing, while doing the cut manually in Premiere.

TRANSCRIBE

1. Save the edited video to my computer.

2. A script I built with Claude Code takes over from there, copies the video into the correct folder, and automatically transcribes the file, generating a transcript.

TITLE AND DESCRIPTION

1. Run the transcript through five different models—Claude, Gemini, Grok, DeepSeek, and ChatGPT—with the same prompt.1

2. Pick whichever headline and description I like best and tweak it myself from there.2

THUMBNAIL

1. Use the thumbnail ideas generated for me, plus my own ideas, to build a thumbnail in Canva. This takes me over an hour at least; I’m not great at digital design. Canva’s AI tools let me auto-expand and transform images until I get something coherent.

2. Upload the draft video to VidIQ, which analyzes it and suggests tweaks to the thumbnail and alternate titles.

3. Go back into Canva and make VidIQ’s suggested changes. I usually go through about three rounds of this until I have a working thumbnail and title.

PUBLISH

1. Tweak the SEO-optimized description with my own wording, or reword anything that doesn’t read well.

2. Upload the video to YouTube, then upload separate copies to Patreon and Spotify.

CLIP

1. Check Spotify first, since their auto-clipper generally picks the best moments.

2. Re-create those clips from scratch in CapCut, since Spotify’s short-form clips can’t be downloaded, reworking the aspect ratio and adding stock footage from Pexels.

3. Run each piece of short-form content through VidIQ to optimize the title and hashtags.

4. I’ve also been experimenting with OpusClip for generating short-form content.

This entire process takes multiple days. I’m effectively a one-woman operation, and I publish two video episodes a week.

NEWSLETTER

Because producing video and podcast content takes up 95% of my time, I don’t have as much left over to write separate original content for my newsletter in every edition. My newsletter functions as a complement to the podcast, and it’s the way I fund the podcast and video content, since I have zero sponsors. When I do write articles or longer pieces, they’re 100% human-written. Usually I’m reporting on a phenomenon or trend I’ve noticed, and to write it I conduct interviews, pull research, and do classic low-tech reporting. I’ve been thinking a lot about agents lately. I’d love to build some kind of agentic system that skims my articles and automatically sends emails from my address reaching out for comments to everyone necessary, but I haven’t built that yet.

BUILD THE TOP OF THE NEWSLETTER

1. Take the SEO-optimized YouTube video description and put it at the top of the newsletter, sometimes tweaking it or adding an opening line or two.

2. Embed the YouTube video below that. This stays above the paywall, and it’s built this way to keep that top section optimized for search.

WHAT I’M READING

A list of headlines and links to articles I’m reading, mostly deep dives and long reads. Below the paywall, no AI involved.

THE NEWS RUNDOWN

1. Curate about 30 to 40 news items I’m following that week, always 100% human-curated.

2. Hand it to Claude to sort into categories, something readers specifically asked for. Claude still isn’t great at this, so it takes some cleanup afterward.

Every item in the rundown is a single sentence with a link back to the original source—something that caught my interest or that I thought was notable or funny. Sometimes that’s a tweet I’m copying, and honestly, I don’t always know if the tweet itself was written by AI. I didn’t write it, so I can’t say for sure. Sometimes it’s a headline; sometimes I write the sentence myself. The most important thing is that I always link back to the original source, so readers can see for themselves where the information came from.

Interview and workflow overview were edited for length and clarity.

Earlier this week, we announced a feature that allows readers to scan text published to Substack to see how much of it is estimated to be written by hand or with AI assistance. We also launched tools for publishers, including the ability to run the program——on drafts prior to publication, disable scanning on a post-by-post basis, and add a “How I make this” statement explaining their creative process to set expectations for their readers. These features do not use publisher content, either through Substack or Pangram, to train generative AI models and are now available on web, iOS, and Android.

Norms around AI use and its disclosure are unsettled. But we have made the assessment that while the use of AI isn’t necessarily a problem, a lack of transparency around it definitely is. Our aim is to help writers get credit for the work that’s theirs and help their audiences make more informed choices about what they spend their time on.

Substack has long been home to brilliant writers and thinkers exploring questions about AI disclosure, making a livelihood through writing, and whether technology can replace human effort in art.

, a columnist at The Economist, is highly bullish on AI’s economic upside but recoiled from AI-written prose: “We should shun AI writing even if it is perfectly bearable to read,” he wrote. Science fiction writer evangelized intention, and said that AI output can’t be art because it isn’t the product of choices. The proposed a Mohs-style scale of AI reliance, from 0 to 10, and menaced, “If you let AI do your writing, I will come to your house and kill you.”

Writers have methodically tested what AI can and can’t generate. ran an experiment to track if an LLM could write the parts of a novel that aren’t the prose itself. Engineer, founder, and former venture capitalist tried to measure the statistical signature of literary style, interested to see if a model could eventually learn to write with it. Literature professor examined two very different approaches to LLM-generated poetry and asked whether either gets anywhere close to greatness: “For poets, edge cases are the poem.” wrote a fictional day-in-the-life in a future AI utopia, and , the named plaintiff in Bartz v. Anthropic, the case that resulted in a $1.5 billion settlement for writers, wrote her own detailed argument against generative AI today.

Writer named an economic reality rather than a spiritual one—that most commercial writing was never really creative expression to begin with, so what’s disappearing is a livelihood, not a soul: “I am less threatened by the presence of bad writing created by robot-equipped dullards than I am by the specter of there being no way to make a living as a writer at all.”

The common thread? We believe that human perspective is an essential ingredient of culture, and this will be true no matter how powerful AI becomes.

In the days since the AI scan feature was announced, we’ve seen many publishers putting the tools to use, and initial responses suggest that transparency is the right first step toward protecting writers and improving the experience for their readers.

Others have raised nuanced concerns about the limitations of labeling and potential downsides for the culture of the community on Substack: the risk of false flags, the limits of what a label can actually capture about a piece of writing, and the potential instinct to scrutinize one another’s process rather than engage with the work itself.

AI tool user wrote a post expressing her concerns about the AI scan, calling it a moral purity test in disguise:

A detection tool might estimate whether AI was involved in producing a piece of text. What it cannot tell you is who had the original thought. Who lived the experience. Who spoke the story aloud, rejected the first version, changed the argument, removed the bad language, restored the humor, moved the paragraphs, rewrote the ending, and edited the entire thing again on the Substack page. It cannot tell you who supplied the life. Seventy years old, and using AI.

We read all of your feedback, which we take seriously as we continue to evolve the product and host open conversation on this topic. Based on your comments, we made a change yesterday so that publishers can disable scanning on a post-by-post basis without having to scan the post first or interact with Pangram at all.

We also know that the use of AI tools is incredibly nuanced, with as many use cases as there are creators on the platform. You can create a “How I make this” statement, visible whenever someone scans a piece of your writing. Many publishers have already drafted their own statements, sharing their views on AI and explaining to their readers how, and whether, they use these tools:

We’re invested in continuing the conversation. Our aim is to help build trust between you and your readers and create an environment that allows you to make the choices that are right for your creative work and your business. Starting next week, we’ll be kicking off a new series, Model Behavior, featuring top writers, creators, and thinkers addressing this conversation and exploring how they work in the age of AI.

And we’d like to continue to hear from all of you: restack, comment, share your “How I make this” statement, or tell us how you think Substack can best support writers and creators as they navigate the muddy waters of AI.

We caught up with veteran British soccer writer, podcaster, and historian of the game on the eve of his sixth World Cup final. Over the past six weeks, he’s been all over the map, filing from Mexico City, Guadalajara, Houston, and Boston for The Guardian, Bloomberg, the Paris Review, and more, while bringing literary dispatches and wry analysis to his own newsletter Wilson’s World (of football). We asked him to document the day he covered the Spain-France semifinal in Dallas and chatted with him about his Substack strategy, how he expanded his subscriber base by 40% over the course of the tournament, and his reckoning with the strange atmosphere at World Cup 2026.

Your sixth world cup! How many matches did you get to this time around?

Fifteen, I think. Maybe 16. I did three in Mexico City, three in Guadalajara, two in Monterrey, so that’s eight. I did four in Dallas, two in Houston, one in Boston. So 15 total!

I also loved your dispatches from the games you caught along the way: watching from hotel bars, or restaurant patios, or catching the Germany-Paraguay penalty shootout at an airport Chili’s.

I wasn’t even in it! I was outside the Chili’s. I was rushing through security to see the end, obviously had to make my flight, and I could see the screens. I was like, “Okay, I can just go over there and watch.” There were maybe about a dozen people there when I got there, and I got there at about 117 minutes. By the end of the penalties there were 60, 70, 80 people standing there. If you’d been selecting the most diverse group of people you could have found, you couldn’t have created a better one. There were a couple of security staff, a pilot, a couple of cleaners, a bloke in a Swiss shirt, loads of people with Mexican shirts, babies in pushchairs, old people in wheelchairs. People who clearly knew exactly what was going on, people who said, “I don’t understand this. What happens next?” It was the great World Cup moment of everybody coming together to watch this exciting denouement of the game.

How does that compare to being in the stadium?

In the stadium you get a much better feel for the game. It’s almost like a native speaker of a language. You have to start speaking a language before you’re 6 or 7 to really understand it. Football’s exactly the same. If you start going to games when you’re 4 or 5, you can smell what’s going to happen. You don’t know why, you can’t explain it, but it’s a very common thing for people who have been going from that age. That sense for a shift in emotional momentum—you get a much better feel for that in the stadium.

Fans at World Cups are not the same as fans in club games. It’s a much more touristy, jolly, happy vibe. There’s a lot of anger at club games. The Spain-France game was weirdly unanxious. Spain was so obviously better that everybody sort of accepted their fate. There was no greater roar to try and rally the French. The French have a slightly strange reputation for not really being a football country. It was only after they won the World Cup in ’98 that the average crowd in the French first division went above 20,000 for the first time. I think it has changed over the last nearly 30 years, but certainly in the late ’90s there was a perception that the French didn’t really know whether they preferred football, rugby, or cycling. You see a self-conscious wackiness about French fans rather than the raging anger you get from England fans.

You’ve written quite a bit about the atmosphere inside the stadiums this time around: the DJ sets, the cheerleaders, the QVC-style entertainment before kickoff. Did this World Cup feel particularly American?

It’s so relentless. From three hours before kickoff, they’re just blasting noise at you and trying to sell you stuff. Things like Dance Cam and Kiss Cam and just showing fans. If that was England, people would be making rude gestures at the camera. There’s no way they’d just be grinning and waving and going along with it. That anarchic attitude the English fan has just doesn’t seem to exist anywhere else, for better or for worse. I do wonder if it’s because everything’s so expensive here that people think, “I’ve spent $5,000 on this. I’ve got to at least convince myself I’m having a good time.” Maybe sticking two fingers up at the camera isn’t the best way to do that.

Did you go into the tournament with a Substack strategy, or did you figure it out as you went?

A bit of both. I had a plan pre–World Cup that I’d do two pieces a week and one of them would be paid. I realized during the World Cup there’s way more to say than that. I deliberately didn’t take on too much freelance work so that ideas I had that didn’t work for The Guardian I could put on Substack. It has worked. My subscriber base has gone up by about 40%, which is a huge increase. There’s a freedom there that I can write to whatever length I want. A lot of it was fumbling around, seeing what worked.

The thing that got me the most new readers was when the Folarin Balogun decision was made, when his suspension for the red card was overturned. I was on a bus between Houston and Dallas, saw the news break on my phone, and thought, “I’ve actually got an hour and a half here. I can just write something, get it out there.” Because it was such an obviously disgraceful decision, I was writing with a real degree of anger and frustration. There’s also a historical precedent for this, in 1962, which I knew about from doing the book [The Power and the Glory], so I was able to bring that in. That combination of historical knowledge plus opinion, that’s when I write best anyway, when I care about something but there’s also some history behind it. It was a story a lot of people were interested in, and I was able to get it out quickly. I must have got a dozen, maybe 20 paid subscribers off the back of that, which for one piece is great.

Why did that piece end up on your newsletter rather than The Guardian?

The Guardian has people who cover the sports politics side of things. It’s not totally impossible they’d have asked me to do it, but they also knew I was on a bus. And they have to pay me for every piece, so they’re quite careful about what they give me. There’s a financial incentive for them to use their contracted staff rather than me.

Would you want to be full-time at The Guardian?

I was full-time at the Financial Times for three years, and it came to an end, and I’ve been freelance ever since. I like the freedom. I like the fact that basically the harder I work, the more money I get. I like that I can do a huge range of different things. I can do the books when I feel like doing the books. I can do podcasts, documentaries. It’s very good to have The Guardian there, and I’m very grateful that they’ve been quite open to me having one foot in the camp and one foot outside. I do a match a week for them and a column a week, so that’s a basic structure to build around. I now do a newsletter for the U.S. market as well. If they wanted me to move fully on staff and give up everything else, the package would have to be extraordinary. People think you have security if you have a staff job, but if you lose that job, you don’t have a safety net. If you’ve got seven or eight different strings holding you up and one of them’s cut, there are six or seven strings still holding you up, and that’s not a bad position to be in.

How significant is the Substack string, financially?

I’ve been running my Substack for 18 months. Pre–World Cup it was a nice way to make a bit of beer money on the side. Now it’s a little bit more serious. It’s certainly not enough to live on, but I’m not devoting 100% of my time to it. It’s a nice contingency from a financial point of view. It’s also useful to have an outlet for stuff I want to write that I don’t have other places to write, and I can make money out of it. It’s nice to know that were something to go wrong with The Guardian, I’m not going to be destitute. Probably if The Guardian did go wrong and I devoted more time to it, those [Substack] numbers would go up and it would be a viable salary.

How do you decide what goes behind your paywall?

Pre–World Cup it was simple: Monday is free, Thursday is paid, nothing more complicated than that. During the World Cup I was essentially going alternate free, paid, free, paid. But some things, like the playlists I did with , the historian, there’d be no point putting that behind a paywall. That’s just a bit of fun. Equally the piece I did going through the most significant goal scored in each minute of a World Cup game—why would you put that behind a paywall? It’s free or it’s nothing. I see that as a way of just getting a bit of traffic. But if there’s a properly argued-through piece, if you give people three or four paragraphs, hopefully that intrigues them enough that they’ll pay for the rest of it. A bit of history, you entice them in with the first few paragraphs and hopefully they get the payoff after that.

As to what my paid subscribers look like, I assume they’re people who know me through my other writing, through my podcast and my books, who just want a bit more. The Substack is at times a bit more personal, a bit less formal. Maybe they feel it’s a bit closer to knowing me rather than being filtered through various editors and newspaper editorial practices. I would imagine they’re people not dissimilar to me who’ve got a quirky interest in football history but also want informed opinion about mainstream stuff.

You mentioned that there’s a sensibility you develop if you start watching the game young. Were you one of those kids?

I was. Sunderland was my team; it’s still my team. My dad was a master at making sure that whatever we were doing on a Saturday afternoon, we were by a radio or the TV by 4:40 to get the results coming in. I went to my first game in October 1982, when I was 6. When I was in my mid-teens, I would go to every Sunderland home game, most of the away games, and often Newcastle home games as well. Looking back, it seems insane. At the time, football in Britain was still quite dangerous, and my parents were just saying, “Yeah, make your own way,”—a seven-hour trip to Swindon and back—“just make sure you try and get back by midnight.” But my dad had done it when he was a kid.

Do you remember how much it cost to go to those matches back then?

Almost nothing. It was £2.50 if you were under 16 to get in. And for the away games, there was a fanzine, and the editor would give us a lift as long as we sold the magazine for him. We’d actually make money! He’d pay us £10 to sell the magazine, we’d get the free lift, and he’d often pay for our tickets as well.

Jonathan Wilson’s World Cup Diary—Tuesday, July 14

I recognise this is not something that’s going to get me a lot of sympathy. Covering the World Cup as a journalist is a great privilege, obviously. I’ve been to 15 matches at this tournament and been paid to do it. It’s not really something to complain about, not even when every day seems to bring fresh problems with wi-fi and travel. But by this stage of the tournament, in my sixth week away from home, I’m exhausted.

After covering Spain’s semi-final win over France, I went to a Mexican restaurant in Dallas with a colleague. We both ordered tacos, at which the waiter gleefully told us it was Taco Tuesday, so you got four for $8. Both of us had the same reaction: “Today’s Tuesday?” After so long on the road, neither of us had any idea, although we both had the same sense that it felt Thursdayish, which I think just means that we’re aware the end is close, just not quite as close as we might like.

In that six weeks, I haven’t had a day off. I think there have been two days when I’ve had more than six hours sleep. Eating well is extremely difficult; there’s a lot of meals grabbed in airports and stadium media centres. Exercise tends to be whatever you can manage in your hotel room.

I’m freelance. I work mainly for the Guardian, and my schedule is largely determined by them. I covered Mexico in the group stage, then Texas in the round of 32 and the last 16 and headed up to Boston for the quarter-final. After that I was supposed to be in New York for the last 10 days, watching the remaining six games on television and working on Football Weekly, the Guardian’s very much daily-during-the-World-Cup football podcast. But I also co-host two podcasts—Libero and It Was What It Was—and, since January last year, I’ve had my Substack.

This week has been unusually challenging. I was in New York at the weekend and hoped to have enough time on the Sunday, when there were no World Cup games, to go to the Mets v Red Sox. But tournaments very rarely give you that opportunity. The Guardian were able to secure three passes for each semi-final, so asked me to fly down to Dallas on Monday for Spain v France. That meant having to pull out of the baseball to finish writing the newsletter I always write for the Guardian’s US edition that goes out on Monday morning and to at least start work on a feature about Lionel Scaloni, the Argentina manager. I sorted out flights and hotel and, midway through the afternoon, went out to Bryant Park to meet an Irish journalist to record a section of a podcast previewing the England v Argentina game. That evening, I’d arranged to meet the Guardian’s US sports editor, whom I’d known years ago in London.

My flight on Monday was from Newark at 12:20. But I had an early start: before I set off for the airport, I had to record a podcast for Sky, speak to a journalist from Reuters, and appear on a BBC radio show. When I got to the airport, I had a bagel and coffee and finished my Scaloni piece. Only when I’d filed did I check my flight, and found it was delayed by four hours. Within 10 minutes, it was four and a half hours late. I checked with American Airlines staff and they suggested rerouting via Charlotte. The flight from Charlotte to Dallas was also delayed because of storms in Texas, then there was a lightning strike in North Carolina, and then, just as we were about to take off, somebody vomited, which meant he had to get off and cleaners had to get on. In the end, I was about seven hours late getting to Dallas, having eaten nothing from the bagel to a bag of Doritos in the hotel bar 13 hours later.

But it wasn’t just food I’d missed; I hadn’t answered any emails from finally getting on the plane at around 6pm Eastern Time. Which meant getting up at 6:30am to go through my inbox, have breakfast, and go through the edits to a piece I’d written for Bloomberg before catching the media shuttle to the stadium at 10am. Kick-off wasn’t till 2pm, but the drive takes around 40 minutes and there’s always stuff to sort out: expenses to file and last-minute research to do.

Since there were three of us at the game, I was writing a colour or analysis piece on France, while my colleagues did the match report and a separate piece on Spain. Given the way the game went, it was a relatively straightforward piece to write, so I was able to file 40 minutes or so after the final whistle and catch the first shuttle back. That could have meant an earlyish night after my tacos, except that the atmosphere had been very strange, so I decided to write a piece for my Substack about that, which happily filled in the time before another BBC interview at 10:15pm for the following morning’s Radio 4 Today programme.

And then, at 11pm, to bed, with the alarm set for 4:45am to get to the airport to catch an early flight to New York to watch the England v Argentina game there and record a podcast about it.

The rest of the week looks brutal, workwise, with five podcasts and a live show at the Bowery Ballroom on Thursday and a couple more podcasts and a column to write on Friday before the traditional journalists’ big meal out two days before the final. Everybody’s running on fumes, but that’s the nature of World Cups. It’s the way it’s meant to be.

Whether you’re spending your Substack summer tinkering with your existing newsletter or podcast or launching your first one, we’re shipping features that make it easier to publish, customize, and distribute your work, and engage with your audience. We look forward to hearing what’s most useful and what you want more of. Here’s the latest.

Paid subscriber Perks

Subscriber Perks are a new feature that lets you give your paid audience something extra beyond traditional paywalled content, like discount codes, downloadable resources, or invites to live sessions. Perks you create will appear under the new “Perks” tab on your publication. It’s another way to thank the paid subscribers who support your work and encourage others to upgrade. This is available to publishers who have payments enabled.

Here are some perks publishers are already offering their paid subscribers:

• ’s U.S. shopping guide

• ’s curated list of people to meet at SXSW London

• ’s six-day meal plan

Learn more about subscriber perks in our Help Center.

Saved Notes

You can now save Notes on iOS and Android directly in the Substack app. Saved Notes live in your Substack profile. Just click on the ⋯ in the top right corner to access them.

This dedicated space for saved Notes within your profile is like your curated reading list, or as put it, the place to revisit a Note that’s an “absolute gem.”

Scheduled Chats

You can now schedule Chat threads just like you schedule Notes and posts. Scheduling chats is a great way to build community by connecting regularly with your audience between posts. Schedule a chat by going to the Chat tab, clicking the orange button to start a new Chat thread, and selecting “Schedule” in the thread settings

Polls

You can now post polls to Substack Notes. Polls are another way to continue the conversation with your audience by surfacing their opinions, preferences, and priorities. It’s just one click for them and can lead to a gold mine of ideas for you.

You can embed a poll in a Note or a post:

• In a Note, click on the Poll icon in the bottom of the Note screen.

• In a post, click “More” on the far right side of the text editor and select Poll from the dropdown menu.

, the writer of , recently restacked another publisher’s writing and polled her own audience to gauge their reaction to a parenting etiquette question. She received over 400 responses.

Text formatting

Superscript and subscript

Both superscript and subscript are now available in the post editor. If your writing regularly includes footnotes, scientific notation, exponents, ordinals (1ˢᵗ), or trademark symbols, select “Superscript” from the text editor dropdown. If you frequently use chemical formulas (H₂O) or mathematical notation (x₁), select “Subscript.” We hope this comes in handy for you deep writers, researchers, and thinkers.

Text colors and highlight text

You can now change colors and highlight text you want your readers to pay extra close attention to. You can find the text colors and highlight feature in the post text editor.

Podcasts

A redesigned podcast player

We made updates to our podcast and video player to increase engagement by giving your audience more controls. Subscribers can now adjust playback speed directly from the player, listen to episodes offline, and set a sleep timer to better control auto-advance behavior.

Podcast distribution support

You can now distribute podcasts hosted anywhere to Substack with the same RSS feed and dynamically inserted ads. Get started here.

Tracking prefixes

You can also now add tracking prefixes directly to your show from your Substack dashboard. Tracking prefixes are third-party tools that give you accurate download data across all listening apps. This feature is a part of a growing toolkit to help you run and grow your podcast business on Substack.

Filter subscriber questions in Chat

If you’re running a live video Q&A with your subscribers, you can now filter the chat to show questions only. It’s available on web, iOS, and Android.

Your video settings all in one place

We’ve unified all your video settings in the Substack editor, making editing and publishing more intuitive for creators. Here are some key changes:

• Podcast controls, free previews, clipping, and other options like transcripts and auto-publish to YouTube now live in one place.

• An improved clipping experience includes full-screen viewing, plus an immersive creation flow with control over captions and layout.

Learn more about podcasts in our Help Center.

MCP for stats and analytics

We’re introducing Model Context Protocol (MCP) support for bestsellers on Substack, offering new ways to understand your publication stats by integrating with tools like Claude and ChatGPT. You can get up-to-date analytics about your publication’s performance, subscribers, and engagement over time.

MCP for stats and analytics is available for bestsellers. Learn more about the Substack MCP in our Help Center.

There’s more to come soon. Let us know what’s working and what else you’d like to see, in a Note, in a post, or by restacking.

has lived many different lives as a host and comedian: one of them centered on the singular conviction that Denzel Washington Is the Greatest Actor of All Time Period, another in service of an institution (the ACLU’s At Liberty), another at the helm of several documentaries and seven seasons anchoring CNN’s prime-time Sunday night slot with his show United Shades of America. He’s now launched Who’s With Me?, a new podcast based on and distributed through his Substack publication of the same name, which he’s grown from an email list of 20,000 to nearly 140,000 subscribers since joining the platform in 2024. The show is not another celebrity podcast, he says, but features a guest list of people he can actually text to invite on: Delroy Lindo, Robert Reich, Ted Danson, Daveed Diggs, Misty Copeland, and more. Made in partnership with Malcom Gladwell’s Pushkin Industries, it’s also a venture he’s owned from day one. We sat down with Kamau to find out how season one is going, ask him about his “white whale” guest, and talk about what it means to own his own work in an industry that’s still trying to decide who it’s for.

You kicked off episode one of the new show by saying, “This is me investing in myself and trying to bet on myself, because the industry is not betting on people like me anymore.” What did you mean by that?

I had one of the great runs in the history of show business. I had seven seasons of a television show at CNN with United Shades of America. That puts me in the showbiz hall of fame. I sort of was aware as it was happening that this was rarefied air that I was in. And then when the show went away, I thought I had plans for my next chapter with another show like that, but the industry sort of turned on those shows. After the murder of George Floyd, there was all this clamor in the industry for “We need to talk to more Black creators and empower them.” In one of those conversations, I got my documentary, 1000% Me: Growing Up Mixed. That came out of a conversation with HBO about “What would you like to work on?” And actually, the project was their idea. And so I got something out of that clamor. A lot of Black creators got the meetings and got things greenlit but didn’t actually get projects. By the time it was time to make the projects, the clamor had gone down.

, who is one of the most great and acclaimed directors of our time, is right here with me on Substack too. I think one of the reasons she did it is because she’s like, “I need to get my own voice out there.” And she had to independently raise money for her last movie that was based on a New York Times bestselling book. I still have three children and an 89-year-old mom and a wife, and I need to make sure we’re all eating every day or as often as we want to. So that’s the big story, and that’s happening all through the industry. I’d had all this life in podcasting, as you said, but I never really had what I would define as my own podcast, where I get to do whatever I want to do every week and follow my own nose.

What did that mean for booking guests for the show?

Most are people that I can reach out to directly. So that, I think, on its face means [the show] is different from most of these quote-unquote celebrity-led podcasts. I’m really proud of the fact that so far it is people I’m either in direct contact with or people where I’m like, “Oh, I’ve always wanted to be in direct contact with that person.” I think about Marc Maron’s podcast [WTF with Marc Maron], which if you’re a comedian is the blueprint. It was very clear at some point Marc went from “These are comedians who I have grudges with that I need to solve” to “This is the A-list celebrity whose movie’s out, and now my podcast is one of the cool stops in town.” Right? And I don’t think there’s anything wrong with that, but I think that I want to at least establish the groundwork of not starting there. I want to start personal.

Do you feel like having a built-in subscriber base who already knows your voice gives you the ability to skip the usual swings for A-list guests?

I mean, I definitely think that… like, if Sydney Sweeney called me...

Would you say yes?

Here’s what I would say: Do you actually know who I am? It’s important to me that the people I sit down with have some sense of who I am, because I’m not an entertainment interviewer, I’m not a celebrity stopper. And if you’re not willing to investigate and do the work, I don’t think I really need to talk to you. Now, my publicist might say differently.

Do you have a white whale guest?

Yes. My white whale guest has been the same white whale guest since I’ve started talking to people professionally. It’s Zack de la Rocha from Rage Against the Machine.

Have you tried to get him?

No, I’ve never sent a thing to Zack de la Rocha. I just got it confirmed about a year ago that he knows who I am, and I was very excited about that because I just think he’s probably in the mountains of Mexico with the revolution or rapping in his house on tracks we’ll never hear. But I’d say I’m big on not trying to make things happen not in their time.

I think there’s also a need for me to sit down with Denzel Washington at some point. I got invited to his AFI tribute years ago and I met him, and he knew who I was. United Shades of America was such a big deal. If you were of a certain age and at that point a CNN watcher, you saw me at some point. And 9:00 on a Sunday, which is when it aired, was a prime time for people to just turn on their TV and go, “Oh, what’s this about?” I just met Jodie Foster recently, and I was blown away that she knew who I was. That 9 p.m. on Sunday on CNN really did a lot of work for me with a certain demographic of people.

Do you feel like you’re still getting in front of new audiences?

I feel like part of the reason that it’s important to stay active on social media is because you never know when your clip is going to get in front of a new audience. So you never know when someone’s going to be scrolling on their phone and go, “Oh, who’s that guy?” People are also regularly going, “Oh, that’s where you are.” “You disappeared. You stopped being on Sunday nights on CNN, and I thought you dropped off the face of the earth.” So I think it’s important to stay in some of these social media spaces, because you never know when you’ll not even find a new audience, but find your old audience.

What’s the clipping strategy for the show?

Chris Rock taught me this years ago. He said, “More people see the trailer than see the movie.” So I’m very aware that on some level you want the clips to convert people to listeners of the podcast, but you’re also aware that a lot of these are just only going to be taken in as content on their own. And so there’s a little bit of pressure to make sure that it actually works on its own so if they never see the podcast, they got something out of it. But even with my clip recently with Ted Danson—we were promoting the Ted Danson episode, and he does this major apology for blackface—I was very aware, and me and the producers were like, “We don’t want to put up a two-minute clip of him apologizing for blackface on the internet ’cause that’s just going to work against all of us.” People are going to argue with that clip in the comments, when [in the episode] he talked for, like, 15 minutes. So what we did is we basically put together a teaser. Like, him sort of going, “Hey, can we talk about that?” And he’s like, “We can. Let’s do it.” I mean, it was done better than that. As a way to go, people will know what this is, or they won’t. But it makes you have to go find the thing. And also for me, he did such a generous thing by apologizing. I didn’t want to weaponize it against him by turning it into a two-minute clip that was going to take out all the nuance.

Has anyone clipped it independently and commented on it?

There have been some clips, yeah, like... TMZ clipped it, which was sort of hilarious. But the thing about it is that even when you go clip it, I’m finding it’s so clear that he’s earnest, that you have to be a real asshole to turn it into something that it’s not.

How did the deal with Pushkin Industries come to be?

So there’s a guy who works at Pushkin who fans of my Denzel Washington podcast will know under the moniker of Black Judgment. I’ve known Justin Richmond since he was a recording engineer at U.C. Berkeley, and he just happened to be assigned to our podcast because I was recording the Denzel podcast at U.C. Berkeley. Justin reached out to me and said, “Hey, if you ever want to get into podcasting again, Pushkin might be interested.” So that’s why the Pushkin thing started. I, of course, knew of Malcolm Gladwell. I read his books. I “blinked,” I “thunked,” I did all the things. So then I had a meeting with them. The biggest thing that is important in any deal, especially at this point in my career, is my joke is no new friends, unless those friends really can let you know that they know who you are. So it’s like I said earlier about Sydney Sweeney wanting to do the podcast. I am not the kind of product—and I think in showbiz we have to think of ourselves as products sometimes—that you can just throw me on anything and it’s going to work. I’ve met with a bunch of different podcast companies, had some good meetings, but I really kept coming back [to Pushkin].

Do you own the show?

It’s funny, I went in going, “I hope they can pay me for this,” and then after the way the industry fell apart, I was like, “Oh, I think I need to own all of it.” Which means I have to pay for this. And so we have a relationship and a partnership, but the ownership of the podcast is mine. I just sort of feel like it’s important to bet on myself, especially at this point in my career and at this point in the history of this industry, and at this point in the history of this country. Like, I can’t be giving away pieces of myself knowing where everything is headed. Not to say that I wouldn’t do that under the right circumstances, but it was just really important to me. Sometimes you accidentally end up owning things because nobody thinks it’s valuable. And then sometimes—like the Denzel podcast I didn’t own, and sometimes I was like, “It is crazy that I don’t own that.” ’Cause nobody else would’ve come up with that idea. Or I didn’t own it. I do now. But to me it’s like, I can’t go through that again, especially when every now and again now that podcasts are being sort of... you’re seeing them on Netflix and Hulu and whatever, and people are getting paid for exclusive deals. And I’m not saying I want to do that, but I want to have the option that if that happens, it benefits my family the most.

How does Substack fit into the ownership piece?

I brought in my audience and then built an audience that was way bigger than the people I brought into Substack. And I was just like, “Oh.” I had an email list, but suddenly the email list was doing something. The regular practice of writing on Substack became a thing that I really enjoyed, and the fact that some people were giving me $5 a month for it gave me the incentive to be up till 2 in the morning sometimes, like, “I gotta get this out.” When I finally decided I’m going to do the podcast, I was like, “Well, I have to name it Who’s With Me,” ’cause the Substack has become such a core part of my creative identity, and I only want to build on that. And I’ve already planted a flag on this Who’s With Me concept on Substack. Instead of coming up with nine different names for things, I think this thing has a longer tail than I realized when we came up with that name. So yeah, for me, the Substack is why the podcast is named Who’s With Me, because I had built this community of people with Who’s With Me, and the podcast is now growing out of that.

You’re distributing the show through Substack—uploading each episode and sending it out to other listening platforms. Why did you set it up this way?

I find it’s great because it creates a natural hub for the podcast. Yes, you can go get it on all these other platforms, but I like the regularity and the ease of saying that if you join me here, then you’ll know when the podcast is coming up. Because as we know, with the other platforms, your favorite podcast might be out today, but you might not think about it, or you might not get an alert about it. So I enjoy the fact that on Substack it’s just another way in which I can reach people and go, “Hey, come out again. One more thing for you.”

You mentioned you came in with an email list. You’re now at 137,000 subscribers. What was the size of the list you started with?

I think I showed up at Substack with 20,000 people on my email list. I was not doing much with my email list, because nobody knew what to do with an email list at the time. I would send out emails very irregularly. And so once I got to Substack, someone was like, “Oh, you gotta do it weekly.” Very early on, I wrote a thing about Tracy Chapman coming back to the Grammys, and that was my first real breakthrough moment, and it taught me a lot. I feel like a lot of being a creator is like, what do you like about yourself, but what do other people like about you? And do you like what they like about you? And if you do, you lean into it. If you don’t, you stop doing it.

You start each episode of Who’s With Me? by giving your guests their flowers. Is there anyone else on Substack right now you’d want to give theirs?

I love doing this. I’m going to start with a guy that I actually helped recruit to Substack, . I came to him as a fan. He’s a combat-sports journalist, and I’m thinking about him right now because he [was] the leading commentator on the UFC White House fight. And Luke is a guy who, because he’s a little bit of a lefty MMA commentator, it puts him in a sort of a desert because there’s not a lot of left-wing MMA commentators. And so he has been able to come to Substack and just be himself. Now I see clips of Luke on CNN and I’m like, that glow-up has happened. He’s on . That has happened because I think he came to Substack and was able to sort of just be himself and not be a guy who was trying not to get his fans mad at him.

I would also say , who was with the Washington Post, is doing a lot of great work as a journalist on Substack. There’s a lot of great journalism on Substack, but I think about her story in particular, because it’s about getting fired from the Washington Post, and she’s now writing about her arbitration. She’s also somebody who, if you fire her, you clearly don’t know what you’re doing as a business. Seeing her spread her wings on Substack is great.

was one of the first Black creators I knew who was on Substack. He was on Substack way before I was. His Substack is I like to bring him up because he’s really doing important work in the Black food space and just in Black organizing in general.

I can keep going. I’m going to miss somebody. But let’s just do those three!

The conversation was edited for length and clarity.

It can be hard to put your finger on what makes a Substack get-together so memorable. The depth of conversation? For sure. The variety of people in one space? Absolutely. But mainly I think it’s the fact that Substack writers and creators have the same shared notion that culture thrives when everyone is allowed to put their ideas out into the world.

This past month, we’ve seen this in action as Substack events popped off around the globe, bringing communities of otherwise unconnected creatives together in person. Hundreds of creators came together for our annual U.K. bestsellers drinks in London. In Paris, Substack’s burgeoning French scene gathered for an evening of drinks and conversation. In Madrid, Substack writers met for a one-of-a-kind writing workshop, complete with typewriters, to inspire their next posts. More and more, publishers are organizing their own meetups for their communities all over the world.

Bringing writers together, no matter where they live, is something we have always set out to do here at Substack. In April, we introduced the ability to translate all short-form content on Substack—one of our most-requested features—in order to bring creators closer to their global communities. Today we’re going one step further, announcing that longer-form posts on Substack can now be translated from English into 15 different languages, and from 100 different languages into English. This means language no longer has to be a barrier for the work you publish.

We’re also announcing new country leaderboards for users based in the U.K., France, Italy, the Netherlands, and Spain, which are among the five fastest-growing markets outside the U.S.

These leaderboards offer a valuable way for audiences to find both established bestsellers and up-and-coming publications in their countries, and we are excited about the opportunities this will bring for these publishers. (If you don’t see your country listed here yet, stay tuned.)

All of this is to say that we are building a truly global economic engine for culture; a place where geography or language should not inhibit your scale and ambition for your community, or how far your ideas can spread.

One in three paid creators now exist outside the U.S., and in Europe alone, Substack creators collectively make $90 million annually. What’s more, we are hearing directly from publishers that their audiences are not only growing; they’re growing across the globe. Take food writer , whose Dutch-language publication already reaches readers in 95 countries. Or French film critic , a top bestseller in our film and TV category for his fascinating take on cinema and culture, or , whose Italian publication tops our global culture list.

Country leaderboards and post translations build on the work that we are already doing internationally, including the expansion of our legal Defender program and our events programming.

If you get time today, do explore the incredible bestselling work on Substack around the world, here. You won’t be disappointed.

Harris grew up in Tulsa, Oklahoma, where she watched melodramas with her aunt, crime capers with her dad, and, at 12, wrote a letter to the local film critic disputing his review of The Other Boleyn Girl. In this season finale of Open Tab, she sat down with Substack’s head of new media, , to talk about studying journalism (and thinking she might break the next Watergate), her four years at New York magazine’s Vulture, and launching on Substack in 2020. They met at Trees Lounge inside the Nitehawk Cinema in Prospect Heights, Brooklyn, one of Harris’s home theaters, sipped tequila gimlets, and filled in the rest.

Hanne: So you have subscription revenue as your core, but you also have a podcast, you do TV writing, you still do some freelance for legacy media, and you do some brand stuff. How do you think about the whole mixed-revenue stream, the business of Hung Up?

Hunter: The newsletter is my job. Everything else feels like something fun, something I feel curious about. But I do feel very seriously that people who read the newsletter are customers, and I am fulfilling my contract with them. I just think it’s the most disrespectful thing in the world to be like, “Okay, maybe it’ll come out, maybe it won’t.” Before I owe anyone else work, I owe them work—the readers. And then the brand stuff is just kind of fun. Sometimes it’s like working a different muscle. Like I’ll edit a TikTok and want to kill myself, because my thumbs are too big and my nails are too long to open CapCut. The podcast started as: I just want to have something with my best friend. And it all kind of feels like an ouroboros, where I’m talking about the same thing again and again. But there are people who read the newsletter but don’t listen to the podcast, and vice versa. And the TV stuff is maybe my dream. But if I could write my own series tomorrow, I would still keep the newsletter, because in the middle of the night I’m like, “I love a girl’s emotional support inner wrist tattoo,” and I need a place to say that.

Hanne: You’ve described yourself as having insane tunnel vision. That when you get one of these obsessions, you can really, really follow it. Why do you think that works for you and your audience?

Hunter: I think we just both have the same disease: being insatiable. I think that’s it. Part of it is growing up as an only child, where I just had to entertain myself a lot. And so I maybe will spend more time with something than other people did. The tunnel vision thing really came from one of my old editors who was like, “You have really bad tunnel vision.”

Hanne: Was it a compliment or an insult?

Hunter: No, it was an insult. She meant it. But then I was like, “Oh, yeah, I totally do.” In every part of my life.

Hanne: What’s the most embarrassing obsession that you’ve ever had tunnel vision about?

Hunter: Charlie Puth. I went through a big Charlie Puth phase. He really was the pop prince. Like, he should have been Justin Bieber of the next generation. And then there was one time that I went to see him in concert at Radio City, and I was singing along to every single song and did not mute my camera. And so everyone heard me singing along. One of my friends still talks about it to this day.

Hanne: How do you think about how much of yourself to bring into a celebrity profile?

Hunter: I think, none. In an ideal world you can get a sense of my curiosities, but it’s not about me. Whenever I read a profile that feels like too much about the writer, I’m like, okay, but what did George Clooney have to say?

And then there’s a real romance when you’re preparing for one, where you read everything about this person, everything they’ve ever said, and then you go into the interview and they are disappointing, just because you’ve built them up in your head. But that disappointment should not show up in the piece. There’s a real moment where you have to become very dispassionate. It’s almost like a breakup, because you really have to break up with your idea of someone and just tell the story as it happened.

Hanne: Is the disappointment because you’ve added something into the picture? Or is it always the same, that they’re more human than you thought?

Hunter: I think it’s just that they are human in general. It’s hard to get to know someone like Julia Roberts and be like, “Oh my god, she’s real. She’s a real person.” It’s honestly like when you go out on a date with someone. A little bit of air has just left, because now you’re real in front of me. You know when someone exists on a page for so long and then it happens, and it’s like: okay, we’re just two people talking.

Hanne: A lot of your writing in Hung Up weaves in your personal experience and relationships. What’s the internal thermometer about when you allow your personal life into your writing?

Hunter: The newsletter is written by me. At first I thought I wanted my friends to contribute and all of that. And then pretty quickly I was like, no. This is mine. I’m just such a perfectionist, I have to have my eyes on every single thing. I’ve grown to love that about the newsletter. I’m a star student, star employee, but a terrible boss. And I’m the only person deciding everything, which is nice.

Hanne: What’s your writing process actually like? You’ve mentioned a number of times that you wake up and you just have to write about something.

Hunter: Basically, yeah. I have a note in my phone of ideas that I think about when I wake up or when I go to sleep. Day to day, I’m quite strict about the scheduling. I have to be up, walk my dog, showered and at the desk by 9:30 at the latest. Then I’ll have a little lunch break, and in the afternoon when I can’t write anymore, I’ll watch a screener or go see a movie. And then I have a big burst of energy around 6, 7, or 8 p.m., and I’ll move locations, sit at the coffee table, and write there.

Hanne: You’re also doing the companion podcast for [the HBO medical drama] The Pitt. That seems like a slightly different muscle set.

Hunter: Something that I like about the newsletter that I hadn’t really considered before is that when I write something, everyone knows it’s coming from Hunter, who’s a Black woman, who’s 31, who lives in Brooklyn, who has a dog that’s a schnoodle but she won’t say that. She will say that she has a poodle mix, because schnoodle sounds insane.

When I was writing for Vulture, writing for a magazine, you don’t always have that context. There’d be times where I’d make a joke about SZA and someone would be like, “Oh my god, this white man is talking down to this Black woman.” It plays differently. With The Pitt podcast, it’s the first time in a while I’ve felt some of that, where people who listen don’t know anything else about me. I am myself, but I’m also kind of on my best behavior, because people might not get every one of my jokes.

Hanne: It sounds a little more like being on a stage than being in the living room hanging out with your Hung Up crew.

Hunter: Totally.

FOOTNOTES

Trees Lounge—Unexpected bar within Nitehawk Cinema in Prospect Heights, Brooklyn.

The Other Boleyn Girl—Panned by the Tulsa World critic. Defended by a 12-year-old Hunter.

Vulture’s Gossip Girl recaps—introduced a Hunter to writing about pop culture on the internet.

The Zendaya cover story for GQ

Charlie Puth—Underrecognized “pop prince” and subject of Hunter’s most “embarrassing” tunnel vision.

The Pitt—Hunter co-hosts the official companion podcast to the hit show.

Ouroboros—Ancient symbol of a snake eating its own tail. Hunter says her newsletter, podcast, and brand work exist in a loop.

Ask Polly—Written by . Hunter’s North Star on Substack. “I could never be so raw, vulnerable, and also kind of moody and mischievous on the page.”

Friends with Money—Nicole Holofcener film in which all the characters are, in Hunter’s words, “absolutely rancid.”

Incredible movie about eating in bed—Meryl Streep, Jack Nicholson, and a bowl of carbonara in Heartburn, based on the semi-autobiographical novel by Nora Ephron.

Today we’re introducing the next phase of Substack’s native sponsorships program, with an inaugural cohort of flagship partners who are collectively investing millions of dollars into creators on Substack. If you are a Substack bestseller who is interested in participating and shaping the program, you can publish your Creator Kit now.

The deal most of the internet offers creators goes something like this: We’ll give you reach if you give us your audience. Perform for the algorithm. Hope for a minority share of a platform’s own revenue, or figure out the money part yourself. Build your following on our platform, under our rules, subject to our priorities—and if any of that changes, good luck.

Most creators accept this deal because they feel like they have no choice. The platforms are where the audiences are. And over time, the system shapes you. You learn to make things the algorithm rewards instead of things you believe in.

Substack is built on a different theory: Give publishers a direct connection to the people who believe in them. Let people pay for the work they value.

We know that model works. Now more than 100,000 publishers make money on Substack through the subscription model. The top 10 collectively make more than $100 million a year, while tens of millions of subscribers across the network give creators the opportunity to build both audience and business in one place.

At the same time, some of the most successful creators have been finding ways to expand their business and better serve their community by partnering with organizations that help them offer more perks, invest more deeply in their editorial, and introduce new features for subscribers.

’s sponsored letter with Hinge ranked as ’s fourth-most-engaged letter in 2024. She wrote about this herself that year: advertisements on Feed Me, done right, are not compromising her audience-first model.

built his own Product Pass—a collection of complementary product access and trials to companies like Granola, valued at more than $30,000 and offered as a perk to his Annual and Insider subscribers.

reimagined one of his most-read essays and brought it to life as a video.

collaborated with a design partner to unveil a redesign for her publication, .

These creators, along with their independent agents and managers, handled this work themselves. They had to figure out the outreach, negotiate the terms, manage the relationships, and handle the logistics, on top of the work of showing up for their subscribers.

Making something great is hard enough. We want to help make the rest easy.

Substack’s native sponsorships program makes great partnerships simple. We’re excited to work with our flagship partners, including Yahoo Scout, Whatnot, Granola, Balenciaga, T-Mobile, Polymarket, and Uber. These forward-thinking brands recognize that some of the most interesting conversations happening on the internet are driven by writers and creators on Substack. They’ll be building with, and investing millions of dollars in, the creators who choose to participate

These are not arbitrarily inserted ads. They are direct partnerships between brands and publishers who have already built robust audience-first businesses.

Creators choose who they work with. They set the creative direction. They keep full editorial independence. Our job is to take care of what they shouldn’t have to—the matchmaking, the infrastructure, the logistics—so they can stay focused on the work.

To help these publishers control their experience with sponsorship-related revenue, we’ve built Creator Kits, a new tool for creating a media kit for potential brand partners, available today to bestsellers. By publishing your Creator Kit, you can let us know you’re interested in brand collaborations. It is also your entry point into what’s coming next: a partnership platform where you will be able to connect directly with brands investing in the Substack creator ecosystem.

Learn More: How do I set up a Creator Kit on Substack?

Subscriptions are the ultimate proof point of an audience-first media business. Sponsorships, when correctly aligned, can amplify the value of the direct relationship between publisher and audience, creating a stronger foundation for a growing business and community.

Other platforms have built a model that rewards performance. We’re building one that rewards trust.

The system should serve the people who use it, not the other way around. For creators, that means helping you make money doing the work you believe in.

Hamish: You’re a newshound, a scoop-getter, a news-breaker, and a tabloid journalist of sorts.

Lachlan: Allegedly.

Hamish: Cut from the cloth of an old-school type of reporter. And that’s kind of special in today’s world, because lots of people are just random opinionators and mouthers-off.

Lachlan: I’m an old-school newshound. Some would say a muckraker. I spend a lot of time meeting and greeting and ingratiating and sourcing. I always say I’m only as good as my sources, and that’s how I get scoops—being out and about, going out into the world and finding out new information. And then coming back, standing it up, tapping it up. And as we would say, putting it in the paper, which is now a newsletter.

Hamish: You were the number two editor at the National Enquirer, and through your work there you discovered that they were essentially paying for stories so that they could kill those stories on behalf of some powerful figures: Donald Trump, Harvey Weinstein.

Lachlan: That’s correct.

Hamish: Tell me, what was it like to write that story and have it out in the world? Because it was complicated, and it involved so much personal stuff and was a big risk for your journalism career.

Lachlan: And legally a big risk, because I was under, and still am, a nondisclosure agreement. That piece was easily the hardest piece I’ve ever had to write, and it wasn’t fun to write it. It’s fun now to have written it and to talk about it. I remember being at the ASMEs, the magazine awards, and it was right around the time that the indictment had come down against Donald Trump, the hush money indictment. I saw Jake Silverstein, the editor of the Times Magazine, there. I didn’t know him. I said, “G’day, mate. I think I’ve got a cracking yarn.” And he said, “Well, let’s follow up, and we’ll meet about it.” I sit down to write it and I thought, “I can’t do this.” I was getting out old files and I was looking through text messages to re-create scenes, and, as I write about in the piece, my father died suddenly during when all of this was happening. I just thought, I can’t go over this stuff again. It’s just too much for me. And for months, I just couldn’t get anything on the page. It actually took me a year to write. Willy Staley [story editor at the New York Times] said, “Why don’t we do this in chapters? You’re good at writing your column, your newsletter. Why don’t we write this in chapters?” And I finally had the confidence knowing that I didn’t have to file 10,000 words, I just had to file a chapter at a time. I sat down and I wrote the first chapter, and I thought, “Okay, I might be able to do this.” It went through the machinery of the Times. They go [para]graph by graph and give you the colonoscopy of fact checking. They call everyone, and they re-report basically the entire piece out. But it took a year for the whole piece to come together. And it’s easily one of the proudest moments I’ve had when it did finally publish and the whole story was out there.

Hamish: Can you explain for the average person what catch-and-kill actually looks like?

Lachlan: It wasn’t a term I was familiar with when I took the gig as executive editor of the National Enquirer. The first year was run-of-the-mill tabloid fare: Jen and Ben. True-crime yarns. Not Pulitzer Prize–winning stuff. But there were yarns we broke that moved the needle.

It was towards the end of that first year where I had a tip from a very good source who calls me on a Sunday and says, “Weinstein is being questioned over a groping allegation in Tribeca, and I can get you the girl.” I immediately called [National Enquirer editor in chief] Dylan Howard and I said, “I’ve got a cracking one here.” And Dylan just immediately said, “Who’s the source?” Something tweaked in me—Why are you just immediately going to that question, as opposed to how do we get this story across the line?” And it was the next day that the Daily News broke it.

After that, Dylan came into my office and said, “We need to offer her a five-figure amount for her story.” And I was like, “We had the scoop yesterday and we didn’t need to pay her. And now you want to give her money to get her story.” And I just remember thinking, “Something’s off with this whole thing.” She doesn’t want paying. She wanted to get the story out. We had the story yesterday.

Hamish: Why did you start Breaker?

Lachlan: You were telling me for years to strike out on my own as an independent media. You were at me for years. And guess what? You were right.

Hamish: Thank you.

Lachlan: At the time, I thought you were mental when you were like, “What are you doing at legacy?” And you were the bloke who kept saying—because you’ve got to remember, The Daily Beast had a newsletter called Confider, which turned out to be an industry must-read—“Why are you doing this for these people? Strike out on your own.” And you said that to me again when I went to the Hollywood Reporter. Which you were right. I should have just gone straight from The Daily Beast and struck out on my own.

I was freelancing, writing for Vanity Fair and THR and The Ankler, and I thought, I could keep freelancing or I could try and create something myself. And getting back to my late old man, he was 41 when he started his business. And this was right around that same age. And I thought, “Fuck it. I’m entrepreneurial. Here is this opportunity to go off and do it.” What’s the worst thing that can happen? I could lose my life savings.

Hamish: But people respect you more for having done it, even if it doesn’t work out. You are actually improving your career prospects by being entrepreneurial in the first place, by showing you’re willing to do something bold and taking on that risk.

Lachlan: Look, my history has been a series of punts, of gambles. Moving to London at 22 and not knowing anyone. Nailing that and going to New York. But it’s been a series of punts, and most of them have paid off in a weird kind of way. And I think the news gods respect that, if you do take a punt. And starting Breaker was a punt. It’s easily the best thing I’ve ever done. I’m working harder than I’ve ever done—16-, 18-hour days, seven days a week. But I’m creating something that, from the readers I speak to and the subscribers I interact with, is special. It’s something that if it’s not out by 8:30 p.m. on a Tuesday and Thursday, they’re texting me, “Where is it? What’s going on with Breaker?”

Hamish: You were starting this company with a partner. It didn’t work out for whatever reasons. What was that aspect of it like for you?

Lachlan: We had a business that wasn’t growing, so that was problematic for obvious reasons. I’m in a runway situation. I have a certain runway of money, and if this business isn’t growing, I’m in a pickle. And that pickle is me sleeping rough. Things got very real. We had to have a real conversation, and that conversation resulted in him going off in one direction and me having to think very carefully about: how do I propel this business forward?

I said to myself, “I have to resurrect this, and I have the fall to do it. The clock is ticking.” And I thought three things. One, you have to put on a killer event. Two, you have to relaunch the pod with a stellar lineup. And three, you have to break stories that are impactful and consequential. If you do all three, you save the business. If you don’t, we are fucked. And guess what? Fear is one hell of a motivator. The second season of the Breaker pod, we launched with Joe Scarborough, we had , , Jeff Fager, David Remnick. A stellar lineup. We went from being in dive bars to two-star Michelin restaurants. I then broke a number of massive yarns, including breaking the Air Puck story—the deal that Puck was acquiring Air Mail. I broke a Murdoch yarn that CNBC picked up. And I put on one hell of a downtown media party. The New York Times came and covered it, wrote a style section piece. And that three-pronged approach saved the business. It led to a wave of subscribers, it led to a wave of revenue, and it led to me getting to Christmas and thinking, “We’re good. We’re going to hit profitability by year one.” And we were able to announce just the other week that Breaker is profitable. And mate, there was a time I didn’t think we were gonna make it. There was a time I’d wake up in the middle of the night and paint the bathroom, 50 shades of puke. [Now] I can sit here in front of you and say, “I have a profitable business.”

Hamish: What do you think your dad would think of you in this situation?

Lachlan: I do think about what he would think, and he would get a kick out of it. I wish he was around to see it. He went off every day at 6 a.m.to Greensborough, in Melbourne, where his accountancy business was. He started his practice repping plumbers and tradies and ended it repping CEOs and footy stars. And I look at that as the trajectory of Breaker. I’m starting off small, and I have high hopes. And mate, I’ve had a ripper run. It’s not time to go at all, it’s fucking far from it. It’s inspiring to me to think back to those last words that he gave me, which were “Do something you love. Just go off and fucking do something you love.” And I love what I do every day. I meet the most amazing people. I get to tell the most amazing stories, and I’m very lucky.

FOOTNOTES

Tom & Jerry’s—Lachlan’s longtime haunt. 288 Elizabeth St., New York City

Breaker—Lachlan’s twice-weekly media newsletter and podcast covering what’s happening in media, power, and culture in downtown Manhattan and beyond.

Sulzberger barbecue—exclusive annual gathering hosted by the New York Times publisher A.G. Sulzberger in upstate New York. Where the Breaker fedora made its debut.

Yarn—a story, a scoop, a tale worth telling.

The National Enquirer—Lachlan was executive editor under Dylan Howard. Owned by American Media Inc. (AMI).

Dino the doorman—The AMI source who claimed Trump had a love child, passed a polygraph on secondhand information, and was paid $30,000 for a story that never ran. The first catch-and-kill Lachlan says he witnessed firsthand.

National Enquirer Shielded Donald Trump From Playboy Model’s Affair Allegation—Wall Street Journal story for which Lachlan was a key anonymous source. He fed the reporters the term “catch and kill” as cover. It ran four days before the election.

What I Saw Working at the National Inquirer—NYT Magazine exposé published in April 2024. Lachlan was under a 13-page NDA while he wrote it.

Jake Silverstein—Editor of the New York Times Magazine, whom Lachlan approached cold at the National Magazine Awards after the Trump hush money indictment came down.

Jodi Kantor, Megan Twohey, and Ronan Farrow—reporters who blew the Weinstein story open in 2017. Their work is what prompted AMI to send Lachlan the legal threat that backfired and convinced him to start talking.

Graydon Carter’s Air Mail—its acquisition by Puck was one of Lachlan’s Breaker scoops.

Royal Melbourne Institute of Technology—Where Lachlan studied journalism, after completing a taxing entrance exam whose results were published in the newspaper. His mom drove to a 7-Eleven the night before to get the early edition.

Hanne: For somebody growing up today in journalism school who might not know what old newsrooms were like, what was the culture?

Joanna: Well, I mean, first of all, they were incredibly noisy because you had typewriters. And I am not exaggerating when I say that you would get seven pieces of paper, seven pieces of carbon paper. You would put it into the typewriter, and you would have to think very carefully about what you wanted to say, because if you made a mistake, you had to either rip the whole thing out and start all over again or you had to correct it seven times. And you would have what was called Tipp-Ex whiteout, where you had to cross it out. So there was more planning ahead of what you were going to write. It was fantastically noisy. Then computers came in, and half the newsroom, largely men, would say, “Well, I’m not going to use a computer. That’s ridiculous. There’s nothing wrong with a typewriter.” And of course, those people just disappeared out of the newsroom. But it was a very fun, lively culture, and you felt like what you were doing was important, because it was a way of getting information to people. And it was tribal, so people read The Guardian, and that was their tribe. They read the Daily Telegraph or the [London] Times, and that was their tribe. And now of course, we’re inundated with individual voices coming at us, which you don’t really have a sense of their tribe necessarily. Of course, you know, there are lots of newspapers still going, but it’s not quite the journey that was curated for you by the older editors.

Hanne: It was presumably pretty male-dominated at the time, those newsrooms?

Joanna: It was very male-dominated. I worked on Fleet Street when I was working on the Daily Telegraph, the legendary Fleet Street. So you had the high courts at one end, you had St. Paul’s [Cathedral] at the other, and in between you had the big British newspapers. And so at the end of the day, all the journalists would roll out of the various papers and congregate in two or three pubs, the best of which was called El Vino, which is still there. But the crazy thing about it was—and this was in the ’80s—that women weren’t allowed to order or pay for drinks.

Hanne: That’s unbelievable.

Joanna: Isn’t it? Of course, now I look back on it through the lens of, you know, feminism, and think: how outrageous. But at the time, me and the smattering of girlfriends I had in the newsroom were like, “Well, this is great.”

Joanna: When I was editor of Cosmo, we got two questions all the time, consistently the entire time I was there, and this is probably going back through time immemorial, through Helen Gurley Brown’s days, which were “How do I have an orgasm?” and “How do I ask for a raise?” Every month, my monthly mailbag, those were the two dominant questions. So those were the two things we were trying to answer.

Hanne: So it wasn’t changing the direction, actually. You were listening to what was already being asked for and leaning more into that.

Joanna: Well, I’m assuming those questions came in before I was there. And it wasn’t “How do I give my husband or my boyfriend an orgasm?” It was like, “How do I have one?” And then it was like, “How do I make more money?” Because there was a sense in which women understood they were probably being underpaid—which they were—and they wanted to have the power to ask for something, and be successful at it.

Hanne: When you left Hearst you said, “My route is being recalculated.” What did you mean?

Joanna: The impact of digital on a magazine company was enormous, and I was, in essence, doing what a lot of editors were doing, which is managing decline. And I have managed decline well. We had declined, in terms of market share, probably less than other people. But at a certain point, there’s a moment when you want to start leaning into growth and doing something fresh. And I had been at Hearst for 12 years, and it felt like, oh, there’s a gap in the clouds here where I can sort of take off. My kids were older, and I’d had an absolute blast, but it wasn’t going to last. You know? I think everybody in magazines knew there was a train driving straight at you called digital, and it was going to mow you down, and it was much less fun than it had been.

Hanne: If you’ve worked hard at a professional career you always have moments where something is changing direction in a way you didn’t expect, or perhaps you did but you weren’t ready for. And I love that idea of leaning into it instead of just accepting it.

Joanna: It’s very easy to get stuck. You see people get stuck all the time, and then you see it’s too late for them to change, and you can’t get out. And so I had a moment in the clouds when I could get out. I had a fantastic time at Hearst. I loved working there. But these are hard jobs, and you can’t build the railroad fast enough to keep the train from mowing you down. Or at least that’s what it felt like in the moment.

And now these magazines don’t exist, you know? They just don’t—the physical product, for the most part, doesn’t exist anymore, and it’s not as luxurious, and it’s not needed as much because it’s impossible to compete with the phone. The phone is a fabulous device. These people that say, “Oh my god, the phones.” I’m like, “What are you talking about?” The phone keeps us connected. It’s fantastic. There’s so many ideas in there. I can do everything on my phone. It’s incredible. And so to keep sort of running after the phone with an old magazine, sort of saying, “It used to be better in my day”—it’s not true. The world has changed. And you want to be part of that change.

Hanne: When you look at the media landscape today, where do you see the most innovation happening?

Joanna: Well, I think the most innovation is happening on platforms like Substack and YouTube, because people are figuring out what works, what people tune in to. And people are feeling more confident in their voices, I think, which means we hear from a lot of voices that we don’t normally hear from, because they’re mediated by media. And some of them are alarming, and some of them are really interesting, and I love the fact that you can get your own audience by having an authentic voice.

[Before] there just weren’t these places for individual voices to go, and so they were trapped within an old media ecosystem that couldn’t pay them enough, that wouldn’t give them direct connection with the reader. And now we have this incredible set of platforms where you get direct connection with the audience. And you get to do what you’re good at without the heavy hand of corporate America squashing you down, which is often what happens.

Hanne: Do you find your voice changing now that it’s on Substack, that you’re unleashed in a different way?

Joanna: A little bit. For me, Substack is a bit like early Twitter. I was a big adopter of Twitter at the beginning. I absolutely loved it. It felt like you were having a conversation with writers. You could discover all sorts of new voices. And since Elon Musk’s taken over, it’s just completely changed. You get this kind of endless negativity coming in, which doesn’t even feel real. It’s not relevant to me. It doesn’t feel real or useful. Whereas Substack, actually, you feel like, “Oh, I can have a conversation with this person. I love the way this person writes. Oh, I can reach out directly to them.” So you have this sense of a real directness of content, which is kind of high.

FOOTNOTES

, 108 Greenwich Ave., New York—Cozy British tearoom and shop owned by Nicola Perry and her daughter, who produces and publishes the shop’s interview series on Substack.

Ginger cake—served warm with custard.

The Junior Yorkshire Post—where Joanna published her first piece at age 10, for which she was paid £2.

The Spectator—where Joanna began her journalism career in 1984.

Fleet Street—London’s historic newspaper row. Home to the Daily Telegraph, where Joanna worked in the late 1980s, along with most of the major British national papers.

El Vino, 47 Fleet Street—Storied wine bar, still open.

Emma Tucker—editor in chief of the Wall Street Journal. She and Joanna covered the same IRA bombing in their early 20s.

Helen Gurley Brown—Cosmo’s transformative longtime editor. Joanna: “She really re-created the modern template for a magazine. Vanity Fair wouldn’t have existed without Helen Gurley Brown, I don’t think.”

—longtime Elle magazine advice columnist. Writes .

—author of Fire and Fury and three subsequent books on Donald Trump. Writes . He and Joanna co-host a podcast three times a week.

—longtime New Yorker satirist, later let go. Now writes on Substack.

The Bold Type—scripted TV series on that was loosely inspired by Joanna’s career.

Since its founding, Substack has sought to create the best possible conditions for cultures of many varieties to flourish online. Doing so often involves difficult trade-offs, but on top of our core model—where we only earn when writers, artists, journalists, musicians, and so on earn—we’ve managed to chart a distinctive course relative to other platforms. We hope that people, their work, and the communities that form around it all can be more real here than has historically been possible elsewhere, where massive scales and advertising models seem to drain reality even from good-faith creators over time.

A few months ago, we shared this vision for what Substack can be: a place where you can build your own corner of the internet. That means your branding, your community, and your rules, without sacrificing the network that helps you grow. Today, we’re excited to announce the next feature in that effort, which we think will make it possible for even more people to be fully themselves and at home on Substack. We call it Reply Rules, and it combines a couple of elements:

1. Anyone can now set their own Reply Rules, which will appear to anyone replying to them: in comments on their posts, in replies to their Notes, or in Chat.

2. There is now a system that learns every time you hide a reply and preemptively hides replies it thinks you would hide yourself (you can always see these and un-hide them, which the system will also learn from).

Soon, this system will read your Reply Rules when you set them and use them as guidance for its actions, in addition to what it sees you do. Our hope is that it gives you more time to focus on what matters: creating the work that encourages people to stop by your corner of the internet in the first place.

Learn how to set up your Reply Rules here.

Your house, your rules

It will come as no surprise to anyone who has followed Substack’s arc over the years that we try to think carefully about how moderation of various kinds can help or hurt writers, artists, journalists, musicians, and other creatives. To us, the following principles are of the utmost importance:

• Putting power in the hands of individuals and communities, rather than platform owners;

• Reducing administrative burdens—it shouldn’t require extensive learning, mastering interfaces, or fiddling with controls to have a good experience; and

• Facilitating clear zones of ownership. Substack may be lightly moderated, but in your house, your rules should apply.

Reply Rules reflect these values, and use contemporary technologies to make it easier than it’s ever been for Substacks to scalably set and maintain the kind of order that matters to them, using natural language and natural behaviors. Take a look at how some creators are already using Reply Rules to shape the conversations in their communities:

Write the rules you want. Hide the content you think shouldn’t be there. Let the system learn from you and, eventually, take much of the burden of this work off your plate.

Reply Rules are available today to all publications with their language set to English. To get started, go to your publication settings.

publishes jasmi.news, where she interviews AI researchers, eavesdrops at San Francisco house parties, and reports what she calls “an anthropology of disruption”—on-the-ground dispatches from how frontier technology is changing culture. At Substack’s recent Once and Future Media Forum, Jasmine shared her perspective on the comparative advantages she and other independent writers and creators hold in the age of AI: what skills are gaining value, which are losing it, and where economies of attention are going as a result. She’s the first to acknowledge that writers and creators hold a wide range of views—concerns, optimism, fears, curiosity — about what AI means for their work. But here she makes the case for why writers are better positioned than they might think, and what they can do to exercise that advantage whether they choose to use AI or not. What follows is a lightly edited transcript of her talk.

When economists debate the future of work, they often ask the question: what will humans’ comparative advantage be? I think the key to understanding what the future of work looks like is not, How can humans race against the machine, how can we generate slop faster than the machines can generate slop? but rather, What are the human strengths, and how can we understand what skills are going to go down in value now that AI has made them commoditized, versus what skills are going to go up in value because they are still scarce and because the machines simply aren’t very good at them yet? I’m going to introduce four ideas, or provocations, that have shaped the way that I think about AI and my own media career.

One: The value of summary will go down, and the value of secrets will go up.

Reporting is the act of taking private knowledge and making it public. The things that people have not said, things in whisper networks, the tacit knowledge, the open secrets that have never been put in the public domain—the journalist manages to pluck them out and make them public. When you persuade a source to tell you about some corporate malfeasance, or you venture to a remote town that few people have ever written about, or you sneak your way into a tiny underground party and talk about all the people who are there, you are working in a space where there is no training data.

That is what is really valuable. There’s a reason that robotic startups are paying thousands of people to strap little cameras to their heads so that they can fold T-shirts all day and try to take in the world from a human point of view. There’s a reason that data companies like Mercor are paying Redditors $100 an hour to write up their niche hobbies and explain the intricacies of being a knitter, or playing Magic the Gathering. There are all these details and tacit knowledge that you only know by doing, that AI hasn’t had access to yet because it’s just not in the data. AI can summarize, and it can remix information already out there, but it can’t see stuff. It can’t feel stuff. It can’t break news. And the thing that writers can uniquely do is all of that. You can go out into the world, and you can take that knowledge and you can make that public or you can sell it, and that is something that is really valuable.

Two: The value of static content will go down, and the value of live interaction will go up.

I don’t think we’re that far from a world where AI can take in any of our writing styles and replicate it to the point where your median reader will not be able to tell the difference, as long as you feed it the original reporting that you’ve gathered and some notes. And that is a scary thing. The thing is, though, that your audience does want to feel connected to you, and they want to know that a person is real and that you are the same person generating the text. There’s a reason why behind-the-scenes videos go really viral now. It’s because people don’t just want to see the final presentation; they want to see all the proof of work behind it.

For a solo creator, doing live interaction, events, podcast interviews, meetups and hangouts—these things prove that there is a life behind the voice. It allows people to make a connection between a living being and the words on the page and shows that the person’s point of view comes from somewhere. That stuff is going to be scarce, it’s going to be irreplaceable, and I think that most writers should be doing a lot more of it. Every time I do a big written and reported piece, afterward I block out about a month to just go to conferences, go on podcasts, and talk to as many people as possible. Some people don’t like that. They feel like it’s marketing, and it’s not the part that they really enjoy. But I think about it as building that connection and also as getting the ideas out to more people. If I care about the ideas, I want everyone to know about them, no matter the format.

Three: The value of bureaucracies will go down, and the value of founders will go up.

Anyone who works at a tech company will know that AI has blurred the lines between roles. Engineers became designers, and designers became engineers. And companies are also getting much smaller because one person at the very early stages can be their own data scientist, programmer, marketer all at the same time. I think it’s the same for media founders. I think that AI is going to offer a lot of value to people who are jacks-of-all-trades.

I’m a generalist. I think a lot of media founders, a lot of creators, this is your strength too. You don’t need an editor; you’re pretty good at editing your own work. You’re pretty good at picking your own stories. You’re pretty good at being your own marketer. And I think that it’s a real boon. I like that AI helps me with reading a contract before I sign it and telling me what to ask questions about. I like that AI can help me fact-check articles and look up the cites for every sentence, that it can clip videos, that it can negotiate speaking fees.

Before, people would say that if you’re a woman negotiating your speaking fees, you should ask a white man you know with a very large ego. I ask ChatGPT, and it’s incredibly good at this. There’s a lot of stuff that I do not want to do, and I really want AI to do it for me. And so I think this is going to be an amazing age for people who are media founders, who are excited about being sort of the directors and owners of their project and who take advantage of technology to do all the other stuff and focus on their creative vision.

Four: The value of polish is going to go down and the value of personal charisma and style and weirdness is going to go up.

There’s this saying that I was told when I once asked a senior media person whether I should take a staff job at a big publication. It was not The New Yorker, to be clear, but he told me that The New Yorker “makes bad writers good, good writers good, and great writers good.” When I wrote for the New York Times business section, I felt like I was basically outputting code syntax. It felt totally LLM-able. The reporting was not. Again, I’m very bullish on reporting—but the writing style itself was basically like you could shove that through Claude and be like, “Go figure it out.” And that was a little bit demoralizing, because I like writing and I like style.

The thing that’s really great, though, is that what every Substacker is already really good at is having a very distinct voice that their readers really feel a connection with. I think that your readers probably don’t mind that there are typos. They don’t mind that you get stuff wrong. That is what the AIs cannot do: being able to talk in the first person, being able to be provocative versus hedging every single little thing.

One thing that a lot of my AI and tech friends don’t really understand is that trust is not about information and its quality alone. It’s about the messenger. And so when they talk about having AGIs that do super-persuasion by writing the most persuasive sentence in the world, I think: I don’t think you understand trust, because it’s not about the sentence. It’s about who says it and their track record and what they’ve told me before. And the stronger your individual brand, the trust you build, the voice you have, the track record that is just yours, the better off you’ll be.

I imagine that some people who hear this might disagree with me on a bunch of things about AI progress. That’s okay. But I think that there are a lot of good reasons to be optimistic as a creator right now, as a writer, as an independent writer in particular, somebody who is not part of an institution and really just doing your own thing.

I live in San Francisco, and all the time I talk to my friends who are working at these AI companies, and they’re working 9-9-6 hours. And I’m like, “Why are you doing this?” And for some people it’s a mission. Other people are like, “I’m going to escape the permanent underclass so that in the post-scarcity utopia, I can finally make art and have a coffee shop.” And I’m like, “Dude, you don’t have to wait. You can literally do that right now.”

I really feel that if someone handed me a UBI check and 24 hours in a day, I would be doing exactly what I do right now. I would be talking to people, going out and seeing stuff, writing about it, talking to people about what I write. I really feel that it’s the best time in the world to be an independent writer, and I’m very glad to get to do it with all of you.

Watch Jasmine’s talk from The Once and Future Media Forum here.

Kelly is also the founding executive editor of Wired, where he spent the better part of the 1990s helping people understand technology as culture. Before that, he was a key editor and publisher at the Whole Earth Review and a central figure at the Whole Earth Catalog, the legendary tools-and-ideas resource that shaped a generation of independent builders and thinkers from the late 1960s through the 1980s. He is the originator of the “1,000 true fans” theory—the idea that a creator with direct access to their audience needs only 1,000 people willing to buy anything they make to sustain a living—one of the most practically influential ideas in independent media. In his conversation with Substack’s head of new media, Hanne Winarsky, he talks about his journey through tech and media and the subjects he writes about for his Substack audience at his newsletter, : taking a prototyping approach to life, why optimism is a daily practice, and some guesses for where we’re headed next.

Hanne: There was no web at the very launch of Wired?

Kevin: The web happened within a year or so of Wired. The first couple of years we were working on it, it was going to be a paper magazine with an online presence. So we started Wired Digital, which was actually in a separate building, and we developed a whole bunch of editors and people, and they were inventing what the media would be like. One of the questions that was really unclear to everybody was frequency. How often do we have to update this? We’re doing a monthly magazine. Are we going to have to update this every month?

Hanne: Oh my gosh. Yes, and then some.

Kevin: The thing that a lot of people did not believe was that people would read online. And secondly, people don’t remember, but in the ’80s, there were a lot of people saying that writing was over. Nobody was going to write. What we learned from the web was: no. People are going to write. Almost any of us writes far, far more words per day than our grandparents ever did. We’re all writers, really.

Hanne: And there’s that optimism again. Part of your thinking about communities and audiences at Wired coalesced into an essay around 2008 called “1,000 True Fans”—an idea that in a lot of ways is very much connected to what Substack is today. Can you describe where it came from?

Kevin: The premise is that if you have direct contact with your audience or your customers, you don’t need millions of them to make a living. If you have a label or a publisher or a studio in between you, then you might need millions. But if you take those away and go directly to them, you just have a much more feasible number to get to. You get $100 per year from 1,000 true fans, you can make it. I defined a true fan as somebody who would purchase anything you made. When I introduced this idea, there weren’t any examples of anybody I could find who was doing that organically.

Hanne: Was your hypothesis at the time that there would be a lot more people doing this?

Kevin: Yeah, I thought the arithmetic made sense. Even the weirdest, wackiest, esoteric idea that only appeals to one in a million people, with 8 billion people in the world, there’s still a thousand people who are going to be into your weird thing. The challenge is going to be finding them and making that connection. I think that’s where the next technology is going to be useful—maybe AI—that would allow you to find your thousand true fans.

Kevin: I talk about inevitabilities in technology. A lot of what we have is inevitable given the whole system. AI is inevitable. Any civilization anywhere in the galaxy that invented electricity and steam engines and motors is going to make AI. But the character of the AI is not inevitable. Quadrupeds as an animal are inevitable on any kind of planet with our kind of gravity, but a zebra is not. The specificity is not inevitable. How it shows up, the particulars, are completely up to us. We have a choice in the particulars, and those choices make a big difference. Who owns AI? Is it public? Is it international? Is it closed? Is it open? How is it financed? All those choices are choices we have. But AI itself is inevitable. Those minds are going to keep coming.

Life is going to continue on. There’s almost nothing we humans could do to eradicate life on the planet. But we can still manage natural systems for our benefit. The same thing with technology. I think we do have to manage it and garden it and steer it. The way to steer technology is through use. You want to embrace technologies and use them, because that’s the only way you get to steer them. If you prohibit them or ban them or refuse them, you don’t get to steer.

Hanne: It’s also the only way you start impacting the particulars, the things you actually control.

Kevin: We cannot think our way to the particulars. I call it “thinkism”—this idea that just thinking about things will solve stuff, [that] thinking about technology, we can figure out what it’s good and bad for. We can’t. We have to actually use it.

Hanne: This systems-level thinking, where do you think it came from? Were you just born with it?

Kevin: I don’t think it began that way. I think it’s something I learned. The way I would describe it now is this prototype approach to the world. What we want to think about is our use of social media right now—we’re still prototyping it. And the idea of prototyping your life rather than deciding what you’re going to do for the rest of your life. You try it for a couple of years and you go on. You prototype everything out of cardboard first. You make one to throw away, as the makers say. The first one you’re just going to throw away anyway.

I’ve collapsed some of that into my idea of “protopia.” We aren’t headed to utopia, where everything’s fine. We’re going to come to a world where things are a little tiny bit better, and we’re just incrementally prototyping our way forward. No massive jumps. Just 1% better, 1% better. That means there could be 49% crap in the world, 49% harm, and everybody knows it. I can make a long list of all the things wrong. But there could be 51% good. That 2% difference is hardly even visible.

Hanne: But it is. We are inching incrementally, prototyping, learning, perhaps painfully. It’s a combination of the immediate now and the very long term. The only way to do anything forever is to do something now, concrete, over and over.

Kevin: You sail forward.

FOOTNOTES

The Interval at Long Now—Fort Mason Center for Arts and Culture, San Francisco.

The Clock of the Long Now—built inside a mountain in West Texas, designed to tick for 10,000 years.

Jeff Bezos—contributed $42 million towards the Clock of the Long Now. Kevin cites him on the competitive advantage of thinking in longer time horizons.

The Whole Earth Catalog—Iconic counterculture magazine and product catalog. Described by Steve Jobs in his 2005 Stanford commencement address as “sort of like Google in paperback form, 35 years before Google came along.”

Woodstock—where Kevin first encountered the Whole Earth Catalog, in a bookstore, in 1969.

Walt Whitman’s Leaves of Grass (1855)—the book that sent Kevin wandering.

The WELL (Whole Earth ’Lectronic Link)—one of the earliest online communities, co-founded by Stephen Brand and Kevin. Among the first places humans encountered flame wars, trolling, and people living with completely different online personas.

The first Artificial Life conference (ALife I)— Held at Los Alamos National Laboratory in 1987, the scientific gathering launched Kevin’s first book. He attended as a journalist and posted live notes to the WELL, “live-blogging before blogging.”

Louis Rossetto—co-founder of Wired, who recruited Kevin with the pitch that the magazine should feel “like it’s been mailed back from the future.”

Wired—launched in March 1993. Kevin served as founding executive editor until 1999. His current title is Senior Maverick.

“1,000 True Fans”—Kevin’s 2008 essay. The math: 1,000 fans who each spend $100 a year = a living.

Kraig Adams—Kevin’s 1,000 true fans example in action. Adams embarks on silent hikes with a drone following him and now sells tickets for fans to walk alongside him in person.

What Technology Wants (2010)—Kevin’s book arguing that technology is not separate from nature but an extension of it. Home of the concept of “the technium,” the self-organizing seventh kingdom of life.

Thinkism—Kevin’s word for the mistaken belief that thinking hard about a technology is sufficient to understand it. He thinks you only get to steer a technology by using it.

Protopia—Kevin’s concept of incremental progress. Not utopia (everything is fine) or dystopia (everything is terrible), but a world that is 1% better, year over year, through persistent prototyping.

Finite and Infinite Games (James Carse, 1986)—A guide to choosing optimism. Finite games have winners and losers and fixed rules; infinite games exist only to keep being played, with as many players as possible. Kevin suggests choosing infinite games wherever you can.

Minority Report (2002)—the Steven Spielberg film for which Kevin served as a futurist adviser.

Twice a month, internet-culture publication logs on with someone extremely online and asks them nearly the same set of questions: What memes are making you laugh? Where do you get your news? Do you text people voice notes? The series is called My Internet, and it’s one of several recurring formats that founders and have built since being laid off and starting their newsletter in 2021. Over the years, they’ve expanded it into a multi-vertical operation, with the free interview series drawing readers in and paid tiers that unlock essays, a Friday media gossip column, and a video series. Kate told us Embedded’s growth has been “a lesson in consistency”: nearly five years of publishing almost every week, building an audience entirely their own.

Kate has made her career in part out of naming what the internet is doing, contributing to our vernacular and comments sections phrases like “millennial pause” (first seen on Embedded) and “rawdogging.” She’s been cited as an expert by the BBC and CBC, and co-hosts ICYMI, Slate’s podcast about internet culture. Today we flip the script on one of the internet’s shrewdest observers, asking Kate to sit for her own Embedded Q&A and talk about the business she’s built around the format.

What’s been your best-performing newsletter post? Why do you think it hit?

It’s never the ones you expect, but this one is far and away Embedded’s most popular post, so much so that it was syndicated and translated into Dutch, and I still get notifications on it at least once a week. As for why it hit, I think you can’t overestimate the value of articulating a simple truth. I can sometimes hold myself back by not writing something purely because I assume it’s too simple or something people already know. But even if people already know something, it’s validating to see it in writing.

Embedded

You might just have to be bored

Embedded is your essential guide to what’s good on the internet, written by Kate Lindsay and edited by Nick Catucci…

Read more

2 years ago · 2273 likes · kate lindsay

You started Embedded on Substack in 2021 with no existing email list. What has kept you going?

When Nick and I got laid off, we decided to start a Substack to keep ourselves sane during another pandemic summer. We essentially treated Embedded like our full-time job while still receiving severance. It was exciting to finally have no rules and explore all types of content, and I think this freedom really fueled us those first few months. But I had also spent much of my early career fighting for success within traditional media without much growth, and ironically, once we went independent, that’s actually when those editors and publications found my work. It’s always been extremely affirming to carve my own path rather than fight for approval within the system.

What have been the biggest moments of growth for Embedded?

I will always remember that it was who gave us our first shout-out in her newsletter, and I think we got 500-something subscribers from that alone. Other than that, Embedded has really been a lesson in consistency. We’ll have pieces that pop off here and there, but almost all of our growth came slow and steady from reliably publishing almost every single week for the past five years.

How has the newsletter fed into your other work?

I see Embedded and ICYMI as practically sisters at this point. Often, I’ll write something for Embedded and not even realize it helped me work out my thoughts for an adjacent episode. Sometimes I’ll write something for Embedded that I know could be extrapolated into an ICYMI episode, but want see how Embedded readers respond first. My piece about the phone social contract is an example of one that ended up doing really well, and so that told me it would likely resonate with the podcast audience as well.

While there’s definitely a lot of overlap in terms of the types of readers and listeners, Embedded will always be my rock. It’s the reason I feel even a marginal sense of safety in an unpredictable media landscape.

How do you and Nick decide what goes behind the paywall?

This is something I’ve never been able to get a read on. I can tell you what hasn’t worked: paywalling interviews, paywalling link roundups, and I don’t think paywalling video has either. But I’m having fun with it and I like the privacy of a smaller audience. Otherwise, the things that blow up in terms of paid conversations are almost never what I expected—except for the launch of media_gossip. That went exactly as I thought, because all of us are incurably nosy and self-interested.

How is building an audience on Substack different from other places on the internet? Do you have any advice?

Every day I am grateful to not be beholden to an algorithm that no one can explain and that changes its whims every other month. It means my advice for how to succeed on Substack isn’t sexy, but it’s real: Write for your readers, and if you don’t have any yet, write the newsletter you want to read. Write it consistently even on the weeks you don’t feel like it. And don’t use AI. If you’re using AI to write, I don’t understand why you’re here.

What’s a recent meme or post that made you laugh?

My friend Jehan and I have a shared language of Stuart Little memes. This is the most recent one to make me laugh, but nothing will ever beat this one:

Where do you tend to get your news?

I do my best to not get it, but it finds me anyway.

What are your favorite newsletters?

I always open , , and on Substack, as well as Garbage Day and Today in Tabs. And then there’s a handful of other newsletters that I should be reading but can’t bring myself to because I’m too jealous.

Do you try to limit your phone use? If so, what methods have been helpful for that?

Yes! Every day is an experiment of how much more I can log off while still being able to do my job. I shared a number of tips here, but the most basic, unglamorous advice is still the most effective: charge your phone far enough away that you can’t use it falling asleep or waking up, do one IRL thing every morning before looking at your screen (truly, even just making coffee), and turn off push notifications. You’re not allowed to complain that xyz doesn’t work for you if you’re not already doing these things as a baseline.

What’s something you’ve observed about the online behavior of Gen Z, millennials, Gen X, and/or boomers?

Unfortunately, observing this one thing about the online behavior of millennials is responsible for my whole career.

Do any of your group chats have a name that you’re willing to share?

There’s “just idiots, swarming,” which is all my friends, “sart of like narmal people,” which is a smaller spinoff from a trip to Ireland, “for making swinging plans,” which is me and my husband and his best friend and my best friend, who are also dating, and then “The Lindsay Family Extended Universe,” which is my immediate family plus the husbands.

What’s your go-to emoji, and what does it mean to you?

I’m using this guy 🫡 a lot these days to end any sentence in which I’ve declared that I’ve even remotely achieved something, like sending an email.

Do you text people voice notes? If not, how do you feel about getting them?

I am pro voice note, but I am glad to finally have a space to complain about how maddening it is that listening to a voice note doesn’t register as activity on an iPhone. If someone sends a particularly long note, my phone often goes dark halfway through, cutting off the message and not saving my place. Then I have to start over and regularly tap random parts of the screen so it doesn’t go back to sleep.

What’s your favorite non-social-media app?

Ancestry.com. People talk about falling into TikTok holes—I fall into Ancestry.com holes. I’ve looked up from researching some great-, great-, great-, great-, great-grandfather and realized it’s 1 a.m. I’ve been trying to learn more about my family’s roots in Scotland, so if anyone else from the McPheeters clan is reading, please reach out, because I’ve hit a dead end in 1668.

Have you recently read an article, book, or social media post about the internet that you’ve found particularly insightful?

Yes, but whenever I do, I have a meltdown over the fact that I didn’t think of it. This post from Max Read is my white whale.

What’s the last thing that brought you joy online?

The r/blackcats subreddit. I have two black cats. Black cats are the best cats, and if you don’t believe me, please spend just one minute in black cats subreddit.

Is there any corner of Substack that you frequent that might surprise us?

I just recently started getting into using recipes from Substackers. I made this clotted cream cake by for my friend Rachel’s birthday, and it’s so simple and perfect and I highly recommend.

With , the media company he founded and now runs on Substack, Ashlee is still writing, reporting, and making films, but with his own shop and team. He says his work gives audiences a window into where the world is going six or seven years before the rest of the culture catches up. In his conversation with Hamish, he talks about what it actually takes to get close to a subject, why he walked away from what he called the best job in media, and the stories and formats he’s building as the bet seems to be paying off.

Hamish: Why are we here at Fred’s Place in Mountain View?

Ashlee: I spent most of my early 20s in the Tenderloin [in San Francisco] bonding with dive bars. It was part of my lifestyle. Fred’s has been here for about 60 years. They go back to the ’50s. And down the road, probably about a mile from here, is where Fairchild Semiconductor was—which was like the first real semiconductor company. There’s always been this part of Silicon Valley culture that I like, which is they were boozers. As the chip industry was starting to explode, they were pushing the limits of physics, they were pushing the limits of chemistry, they were all super-competitive at their companies. But as engineers are wont to do, they couldn’t help themselves but come to the bar and reveal how they’d just gotten past something that was challenging the whole industry. They would all share this knowledge, and then the whole industry would move forward. Even today, you have AI companies in this multi-trillion-dollar life-and-death struggle. And those guys don’t go to bars, but they meet up and share their takeaways. They do hot yoga and then share how they figured something out. The same thing, though. So I thought, this bar will be symbolic of those roots and traditions.

Hamish: Ten years ago, you published the first good biography of Elon Musk, which became a massive bestseller and a phenomenon in its own right. You got a lot of access to Elon through the writing of that book. It must have been hard to convince him to give you that time in the first place. Can you tell me about what that experience was like, working on a book like that while giving access to the principal—and this particular kind of principal, who’s prickly?

Ashlee: It was really strange. I’d done a big magazine story on him—that was the first time I’d met him—and we’d got along okay. There was some kind of rapport, and that’s what made me a little bit confident about doing the book. But when I told him what I was doing, he said, “No, I’m not going to participate. I’m not going to help you.” So I spent two years interviewing hundreds of people. Huge chunks of them would report back to Elon. I always thought it was going to work out okay, because he wasn’t actively telling people not to talk to me. He wasn’t making it miserable, which would’ve made life a lot harder. Back then, he was already really litigious. People were afraid of him. Nobody had ever written anything truly revealing. He was kind of the weirdo, almost like a circus freak. I’d come into all these meetings and everyone was like, “He’s going to sue me. I don’t want to talk.” It was really hard for a couple of years.

Then one day I was actually ready to start writing, done with all my interviews. He must have some sixth sense, because it was almost in that moment he called. Elon Musk on my caller ID. I had a landline back then. He said, “You’ve been way more persistent than I ever imagined. I’ll do interviews with you if I can read the book before it comes out and make changes.” I said, “Well, I’m not going to do that. Let’s have dinner and hash it out.” It was one of those moments where he’d either say yes or no. Right there on the spot, he said, “Okay, fine. We’ll do one interview a month for as long as you feel like you need.” Which was incredibly fair.

So we’d meet for dinner once a month. Some dinners were an hour, some were four hours—just depended on his schedule and how things were going. It was totally different days. We’d show up to restaurants in Mountain View, Palo Alto. He’d walk in by himself, sit down at the table. No security, nothing. He had a driver, but the driver didn’t even come in. And nobody in the restaurant seemed to notice who he was.

Hamish: So you got a good book out of it, sold 6 or 7 million copies. What was his response like when it came out?

Ashlee: It was funny. I made sure all the books were on boats heading to stores—about five or six days before it was going to be in stores. I just wanted everything to be where he couldn’t undo it, file a lawsuit and block it or something. But he had spent so much time and been really fair, and it felt like he should read it first. So I sent him a PDF the week before it came out, went to bed, and woke up to this stream of emails. He was basically live-blogging the book as he went through it. He’s always been hung up on the Tesla founding question. Marc Tarpenning and Martin Eberhard, the original founders, would say they founded Tesla. Elon would say, “No, I founded Tesla.” When you look at it, they had filed the paperwork, they were working on it. Would Tesla exist without Elon? Definitely not.

Hamish: Especially not in the way that it currently exists.

Ashlee: No way. In the fact-checking process I told him, “Elon, I am going to say that Marc and Martin founded the company. There is no way around this.” He said, “I understand.” And then in the emails, he’s going off about it again. But otherwise he was okay—really just two things upset him. I’d written about when he and his brother Kimbal were coming out here to start Zip2 and had gotten a used BMW. Kimbal told me he bought it with money from painting houses. Elon said he bought it. I told them they could fight about that. The other thing was a quote from an engineer saying Elon takes too much credit for the engineering at SpaceX. [Elon] said, “You wrote that I take too much credit.” I said, “I didn’t write that, Elon. That’s a quote from an engineer. He’s allowed to have his opinion.” Those were the things he was upset about. Otherwise, fine. He actually sent me an email—which I saved in case things got litigious—saying the book was 95% accurate. For Elon, who already hated journalists, that was incredible.

Hamish: I remember you telling me that at the time. I was like, “Well, that’s an amazing result.”

Ashlee: And it was mostly okay. Then about a week later, the Washington Post did a story: the 27 most outrageous things from the book. A big chunk of it was about what a pain in the ass he was to work for. Funny thing is, when he’d read the book, none of that had really fazed him. He’s actually kind of proud of being a tough boss. But then I think when he saw how the world was reacting to it—Tesla was just starting to get a little competition, hiring was a big thing—I think he worried people weren’t going to want to come work for him. And he just flipped the switch.

Hamish: So a week after he gave you the 95% mark, there’s a press reaction, and then he reacts in the press.

Ashlee: Yeah. He starts saying things—there’s the Google acquisition thing. He’s like, “Who told you that?” I said, “Elon, you know who told me that.” And that was the first time I really experienced firsthand some of what I’d heard about. Emails saying things like, “You’re an asshole. I’m going to destroy your life.” I figured he needed to vent. But then a friend inside Tesla told me, “He’s just asked me to find the world’s best libel lawyer.” And I think—I’ve never confirmed this with Elon—but I think he did ask somebody whether it was physically possible to buy every copy of the book worldwide and make it disappear.

Hamish: Did he know publishers can print new copies?

Ashlee: He knew. He was sending me all this stuff, but he knew. And it was frightening. He wasn’t the richest person in the world, but he had about $4 billion. Part of me thought, “Any of this is good. If he sues me, it’s fantastic, I’ll just sell more copies.” But then you think, “He might actually bankrupt me. I don’t know if the publishers will have my back.” I think he was going through the same calculus—like, “I’m going to bash him, but how much do I want to go? It’s only going to get him more publicity.” We didn’t speak at all for about three years—2015 to 2018. Total incommunicado. Every now and then I’d drop him a note, or SpaceX would do a launch and I’d say congratulations. Nothing really came back.

Then around 2018, I was in New Zealand. I was staying at an Airbnb, and same thing—Elon Musk calling on my phone. The last thing he had said to me was something like, “I want you to die.” And he’s like, “Hey, you’re in New Zealand. I’ve never been. I always wanted to reenact the FBI raid on Kim Dotcom.” That was the first thing out of his mouth. I was like, “Okay, we’re not going to talk about what has transpired.” Tesla was just getting out of the worst of its production hell, and he said, “Look, you’re one of the few people on earth who actually knows the history of this company and what it would take to get through this. Do you want to come speak to all the people who worked on it?” I’d basically stopped reporting on anything SpaceX, Tesla, Elon—PTSD, I just didn’t want to do it. But I said, “Okay, this is pretty good.” And then we just shot the shit for a bit, totally as if nothing had ever happened. That started to open things back up. We just started dropping notes every now and then—Twitter DMs, I think. And then he sent something to the effect of “I understand now what this book did.” Basically: you did a good job. Whatever had happened, he seemed to have gotten over it.

Hamish: You started Core Memory: it’s video, it’s shows, it’s documentary, it’s podcasts on video, interviews, scoops, feature writing—which is a lot. You’ve started hiring people, you’re building up a new kind of institution. What is that institution you’re trying to build?

Ashlee: I think what we’re giving the audience is [a window into] six or seven years out of where the world is going. Because I’ve done this for so long and know so many people, you get to ride along on this journey and have this window into that.

Hamish: You’re six or seven years ahead of what mainstream culture is going to catch up on?

Ashlee: Yeah, especially where tech is going. We get to transport you into where the future is heading. I enjoy eccentric, weird people and I’m not terribly judgmental of them. I like people to hear what those kinds of people think, and then you can make up your own mind about whether that’s horrible or good or interesting. I still have this conversation—and it’s like, “We would really like to see this with the New York Times or the Bloomberg masthead on it.” And I’m like, “Okay, that’s not going to happen. Do you understand that I’ve collected all the world’s people that you actually care about into one spot?” Even from the first month I started on Substack—I know how many readers I had, I had all the Bloomberg stats, [and] people grossly overestimate how many views stories on some of those platforms are getting—from the first month, we were doing like six, seven, eight times as many on Core Memory on Substack.

Hamish: People who don’t know the media as well over-optimize for brands that were prestigious in the last century, not knowing those outlets are not reaching a wide audience—not reaching the right audience.

Ashlee: I’ve got a story I’ve been haggling about with someone right now, and they want the Times or Bloomberg on it because they’re like, “We want SEO for jobs, for new hires.” I’m like, “Do you know how the internet works? Everyone on earth is going to read this story.” Sometimes I feel like the PR people are still in that old world. Because what they’re saying just makes no objective sense.

Hamish: To their defense, the world has changed fast. YouTube taking over televisions, taking over the living room—which is now a true, undeniable thing—happened pretty quickly. At most you could say it’s been 10 years, but even 10 years is a short time given the whole life of media. And people who are in the industries that still write about themselves are so invested in that way of being. I subscribe to all the media newsletters. The degree to which they freak out over who’s running a terrestrial television station is absurd relative to its actual influence and relevance.

Ashlee: Yeah. When we first started our YouTube channel and I saw that 65% were watching on TV, that blew me away.

Hamish: What has changed for you, going from being an employed journalist at institutions to being an owner?

Ashlee: [It’s] super-weird. Exhilarating. It’s been an incredible amount of work. Just to get this off the ground, I had to be the face of things—people were coming for my writing voice, my video voice. I’d spent all these years building some kind of reputation. I’m hiring writers, we’re having other people doing video and podcasts. That’s the way it should go, because I want to build a bigger thing. So this first year has been exhilarating and a lot of work.

I had what I think was the best job in media. Bloomberg paid me really well to do whatever I wanted. I got to talk to the world’s most fascinating people in depth. I had the last cushy magazine writer job. I could go to Ukraine—I didn’t even have to clear it with anyone. I could hang out there for two weeks, take a year to file the story. No one said anything. That used to be the norm for a lot of people. I probably might literally be the last person to do that. So it was a hard job to walk away from. But from day one [on Substack], you write a story and you see people read it, you get feedback, you see money come in for your effort. It’s totally different to a paycheck. And then we’ve been building this team. I wish I’d done this a lot sooner, because I think this was always kind of in me. You do have to be a little bit of an entrepreneur. I was always that way—always doing books on the side, documentaries on the side. In literally four days it’ll be a year since we started. We’ve launched so much, and I wouldn’t go back.

Hamish: It’s impressive to see you here with such energy on a Tuesday morning in a bar in Mountain View, given how much you take on. You are writing a lot, reporting a lot, making videos, making documentaries, running a company. I salute that. Thanks for showing the way for other people.

Ashlee: We’re not even at noon yet. We still have time to do more shots. Cheers, man. Cheers.

FOOTNOTES

Fred’s Place, Mountain View, California—Silicon Valley watering hole where the early chip industry’s best-kept secrets had a way of coming out after the second round.

Fred’s Special—a PBR and a shot of Old Crow

Fairchild Semiconductor—The birthplace of Silicon Valley, just a few minutes down the road.

Robert Noyce and Gordon Moore—Worked at Fairchild before leaving to found Intel.

Geek Silicon Valley—Ashlee’s first book.

Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future (2015)—Ashlee’s biography. The first serious account of Musk’s life and companies.

The Simpsons, “The Musk Who Fell to Earth”

Zip2—Elon and Kimbal Musk’s first company. Also the source of an unresolved dispute about who paid for a used BMW.

Kim Dotcom—Internet entrepreneur, subject of a dramatic 2012 FBI raid on his New Zealand mansion. The first thing Elon said when he called Ashlee out of the blue in 2018, after three years of silence, was that he’d always wanted to reenact it.

Rocket Lab/Peter Beck—New Zealand rocket company and its founder, from Invercargill. Ashlee did a full road trip following Beck’s life, which became When the Heavens Went on Sale and Wild Wild Space for HBO.

Neuralink—Elon’s brain-computer interface company. Ashlee has had exclusive access for years and is now making a documentary through Core Memory.

Hello World (Bloomberg)—Ashlee’s travel-tech documentary series. Emmy-nominated in its first year. By far Bloomberg’s most-watched show, by a factor Ashlee describes as roughly 10,000x.

EVE Online—A cultish, ruleless, multi-player space battle game that started in Iceland.

Bryan Johnson—Longevity entrepreneur. Subject of Ashlee’s documentary Don’t Die: The Man Who Wants to Live Forever (Netflix).

Kambo—A purgative ritual using secretions from the giant monkey frog. Ashlee underwent a ceremony while filming (“the best nap of [his] life”).

George Hotz—Hacker who built a DIY self-driving car in his garage. Ashlee broke the story, then rode in the car on what turned out to be its first freeway run.

Zoox—Autonomous vehicle company. Ashlee did an early ride from Palo Alto to San Francisco.

Substack for Media Founders

is a professor of marketing at NYU Stern School of Business, a serial entrepreneur, and, for the past decade, a writer, podcaster and media founder. No Mercy / No Malice, the weekly newsletter he started as a testing ground for book chapters, now goes out to more than 400,000 subscribers, and his media business, , generates roughly $20 million a year in podcast revenue across his portfolio. His reach among the 25-to-54 demographic, he told us, beats the most-watched shows on CNBC.

No Mercy No Malice lived for most of its life passed around a series of email platforms that, as his team describes it, were built for enterprise marketing departments. For the year and a half before they came to Substack, another newsletter, Prof G Markets, was running on beehiiv. In March, the team made the decision to consolidate everything under one roof, bringing a full portfolio of newsletters, video, livestreams, and new subscriber-only content to Substack. In the two months since, they’ve launched three new newsletters and are preparing to debut The Week, a Friday roundup across the Prof G universe. Starting May 27, of Raging Moderates will be co-hosting a weekly livestream with of , their first Substack-exclusive show. “For the first time,” his team told us, “we’re supported by a platform purpose-built for content creators.”

We sat down with Galloway after his first two months on the platform to hear what this subscription revenue has unlocked for him and why he projects that Prof G Media will reach $1 million in ARR on Substack by the end of the year. He was characteristically direct about where media is going and about what it actually costs creators to build on platforms that hold the leverage—where your margin, as he puts it, is their opportunity. He is also honest about what’s hard, what he hasn’t figured out yet, and why he thinks the real test is still ahead.

You’ve been publishing the first of your weekly newsletters, No Mercy / No Malice, for what will be 10 years this summer. What were you first hoping to build when you started?

I just enjoy writing, and I used the newsletter as a kind of petri dish or incubator for chapters for a book. I would have a thought about something and just write. It was literally me at midnight on a Thursday writing something. Usually the top was business-related and the bottom was more personal. It was me punching out something Thursday night as a means of exploration, and it was just cathartic.

Did weaving in personal stories feel intuitive to you from the start?

I enjoy writing about family and my sons. I sometimes write about topics that upset people, or people find my content not in line with what they were expecting, or sometimes I just get it wrong. There have been a couple of seminal business moments [in the newsletter]. I wrote a piece saying WeWork was ridiculous. I got the S1 and wrote up an assessment saying it was a ridiculous idea that this company was going public and I think we’re credited with being one of the forces that stopped the IPO. So there have been some important business moments. But immediately it was obvious that the thing that resonates with people is the personal stories. The most-read post I’ve ever published was a post I wrote about putting my dog down. There’s a wide space for men of my age to talk about their emotions.

The WeWork story makes me think about risk-taking and being publicly outspoken. How do you evaluate what risks are worth taking?

I don’t do a risk assessment. I believe what Sam Harris said: if you have economic security and people who love you unconditionally, you have an obligation to speak your mind. I think when I say something off-mark or wrong, that’s what people enjoy the most, because it gives them a chance to weigh in. I try to write as if the only people who are going to read it are my kids in 20 or 30 years. I want them to understand me better and the world a little bit better. But I try—I can’t always say I do it—I try mostly to ignore the comments. I talk about money, about a lot of my personal failings. I know it resonates with people. There’s a real danger in getting too caught up in thinking about what your audience is going to think of what you’re writing, as opposed to what you actually think is going on.

If not the audience, who serves as a check on you?

You need [checks and balances]. It’s important to reflect. Prof G Media is 27 people, and there are a lot of people in the company who tell me when I’m wrong or disagree with me. The newsletter has evolved dramatically. As my following grew, the number of people working on it grew, because now it involves a lot of data. I take the responsibility seriously that 400,000 people are reading it, not 400. You have a responsibility to do more fact-checking and review it more carefully. It used to be literally me at midnight on a Thursday giving myself 90 minutes to bang something out, and publishing it with the typos and a few charts. Now there are probably three or four people who touch it before it goes out. Graphics. It gets a host read-over. It’s its own podcast now. I have a lot of people who, quite frankly, save me from myself on a regular basis.

You built out your consulting firm, L2, specifically to maximize enterprise value, then sold at a significant multiple. Is that a model you’re trying to replicate with Prof G Media?

When I was 26 in business school, I started a strategy firm. After about eight or 10 years, I wanted out. We were doing $10 million in revenue. I sold for $33 million—3.3 times revenues—which is fine, but it was transactional revenue, not recurring revenue. When I started L2, I got a study from Deloitte that had looked at outcomes of private company transactions. They sussed out that companies whose exit multiple was in the top decile typically had four features: recurring revenue, they owned a niche, they had defensible IP, and they were international. So from day one, I set up L2 that way. Instead of charging Nike $800,000 for an engagement, I charged them half a million dollars a year for a quarterly membership.That company got bought for eight times revenues.

With Prof G Media, to be blunt, I’m economically secure. I want to do something I enjoy. But the business is doing really well, and I recognize that people working at Prof G want to have their own houses and cars and college funds. About two years ago, I started thinking there’s enterprise value here. Key to that business is subscription revenue.

Our business does about $20 million top line in podcast revenues, but that business has a multiple of probably two to three times. We just started on Substack and wanted a subscription offering. My guess is we’ll be at an ARR of about a million dollars by the end of the year. That revenue has probably a four to six multiple. In addition, the entire company trades at a higher multiple when subscription revenue is growing faster than your core business. Substack’s role for us was to diversify the revenue mix and create a more valuable one. That’s the entire rationale and motivation for going on Substack.

How would you describe what you’re building on Substack?

We found on YouTube and other platforms, you have to be pretty vertically focused. What we wanted with Substack was a repository for everything we do, because we try to bring a voice of education and insight. We want people to learn and feel like they’re getting real insight, and also entertainment. We try to be funny, irreverent. We wanted a repository where someone could come for all things from Prof G Media.

The two biggest subscriber drivers so far have been our interview with and ’s deep dive on storytelling—she puts together all my decks for my presentations. We’re still learning. I don’t know if I would have guessed those things would drive subscriptions. We’re adding about 150 paid subscribers a week, and a lot more unpaid. Have we cracked this nut? I don’t think so. We’re five or six weeks in. We look at people we admire, like or , and we try to understand what the secret sauce is. What about our content will drive subscriptions? We’re absolutely still in learning mode.

Is it right that this is the first time you’ve ever asked anyone to pay for anything Prof G–related?

I think that’s right, we’ve never asked anyone to pay for anything. It’s always been advertising-driven. When we started Prof G Media, all the podcasts and newsletters were nothing but a marketing funnel for my speaking business. The speaking business was three to four million dollars. The entire media and book business was a million dollars. Now the speaking business is two to three million—I just don’t want to travel as much—and the media business is a $20-million business. But when we first started, all the media was top-of-the-funnel marketing for speaking gigs.

How did you think about what the paid product should be?

We’re still trying to figure that out. You have to offer a ton of value. I think if you have an existing brand as we did, at least initially you’re going to come out of the gate strong because you’re monetizing goodwill, not necessarily the product offering itself. I think I could say to people, “Just help us out, everything’s for free, but subscribe”—and I think we’d get 5,000 subscribers because a lot of people like what we’re doing. But that’s not sustainable.

I’m constantly telling my team: these are the salad days. These are superfans. The real test will be after you have 10,000 subscribers and you’re trying to say to someone, “This is definitely worth $200.” When I look at what people who are successful on Substack in terms of paid subscriptions are offering, they’re just offering a lot of proprietary content. I think anyone who’s making more than a million dollars a year on Substack is exceptionally talented and exceptionally hardworking.

You’ve written a lot about platform dependency and the way intermediaries extract value from creators over time. How does all of that factor into why you’re building here?

I know several people who make their living off Instagram, and I know exactly what’s going to happen to them. These companies will let you grow to a certain amount, and then your margin is their opportunity. YouTube’s a little bit better—they have a revenue share model. But the reason I’ve leaned heavily into podcasting is that there’s so much competition in audio that no one platform—Amazon, Apple, Spotify—can extract the kind of rents that others do. If I put out a podcast, what do I get on Spotify? About 97%. If I had a show on MSNBC, they’d be taking 95% of the revenue for access to that distribution.

If we post something on YouTube, they decide what runs on the right rail. They decide what video comes up next. There’s not a lot of branding that can happen. They decide what you see next. Anyone who is totally dependent on a monopoly or oligopoly should just assume at some point they will turn the tables on you. I was on the board of the New York Times, and we had About.com, a content farm that would do something on, say, cooking, get a ton of traffic, have ads displayed, optimized for Google. One night we woke up and our revenues were down 60% because Google decided they didn’t want to send traffic to About.com. When you’re dealing with an oligopoly, just assume that at some point they will turn the tables on you. I’ve never wanted to build a business on YouTube, TikTok, or Meta. I see that as marketing to drive people to other channels where the split is more favorable towards the creator.

You have a reach that rivals most legacy media organizations. What do you make of that?

I can show you numbers that we’re reaching more people in the core demographic than any show on CNBC. The average age of a CNBC viewer is 63. The average age of a Prof G Markets listener is 34. On Prof G Markets, between video and audio, we’ll get about 300,000 views and listens. That’s 200,000 people in the core demographic, 25 to 54. The most popular CNBC show gets between 300,000 and 500,000, and 30% are in the core demo. We get $45 CPMs for advertisers. CNN gets around $13. The average age of a CNN viewer is 67. It’s 69 for Fox. Sixty-four for CNBC. These direct-to-consumer media companies that can hold onto the majority of the revenue, reinvest back into the content, and reach a younger audience—does anyone under 40 even turn on a TV anymore unless it’s to watch a streaming service?

Traditional media is still a very profitable business, but every minute of every day it’s leaking viewers, advertisers, and revenue to something more authentic that bubbles up organically. The death of traditional media has probably been exaggerated. It’ll die slower than people think. But there does appear to be a pretty big market for whatever you’d call alternative media.

Podcasts are essentially TV shows with a lower-cost means of production. Forty percent of our views on Prof G Markets are on TV, streamed through YouTube. Effectively, podcasts have become TV shows where you get 80% of a TV show for 10% of the price. A million-dollar podcast can be profitable. There’s no such thing as a million-dollar TV show in terms of production value that’s profitable.

Stephen Colbert is the best example. Colbert makes $60 million a year but costs $100 million. [When he leaves CBS] he’ll go to a podcast, take the six or dozen most talented people, make $20 million and clear $15 [million] in EBITDA. The arbitrage is dramatic. Podcasts are becoming TV shows that are almost as rewarding, almost as well-produced, and cost a lot less—so the creator holds onto a lot more of the revenue.

You said you have 27 people across all the Prof G Properties. How have you thought about who to hire and how to keep them?

I’ve always been an operator and the CEO of the companies I’ve started. The difference here is I no longer wanted to be the operator. I just wanted to be the talent. I wanted to hire people who could run the business so I could focus on writing, speaking, presenting, and podcasting. My core competence is storytelling. My superpower is finding and retaining really talented people. The woman who runs Prof G Media, Katherine, I’ve worked with for 15 years. Our chief growth officer I’ve worked with for a decade. My CTO and head of engineering I’ve worked with for 11 years. The team with the best players wins. I’m very proud of retention. We have a general cultural value that’s important to me, and that is we overcompensate. My aim is to pay 50% above market. We have a minimum wage of $100,000 a year for full-time employees and $50 an hour for part-time employees. Most people make substantially more than that. The median age is 26, and the average compensation is about $200,000. I spent my whole life trying to get rich, and I’m still trying to get richer, but a close second is trying to provide economic security for other people. Compensating well is a big cultural value for us, and quite frankly it’s a decent business strategy, because if you have the capital and the business to do it, it results in higher retention. In the eight or nine years Prof G Media has been around, I think one or two people have left voluntarily.

What do you think people are getting wrong right now in business, in tech, in society?

I think AI, from a valuation standpoint and a labor destruction standpoint, has been vastly overhyped. I think the catastrophizing about a labor apocalypse is a fundraising technique, to convince corporations they should continue to spend the millions or billions these companies need them to spend. AI has not come up with a lot of different moisturizers or cooler furniture. The only way they can justify these valuations is if they convince companies you can have the same revenue with 20% fewer employees in the next 24 months. I believe, over the medium and long term, AI will create more jobs than it destroys. I think the valuations are unsustainable. I think we’re going to see a similar drawdown as the dot-com implosion—the technology will survive, the companies that are really seminal will survive, but I’ve been to this movie before.

How are you thinking about AI internally, for content and for the business?

It’s not that disciplined or strategic. We have several younger associates who are very facile with AI, and we’re constantly challenging people to figure out how to be more productive around content production leveraging AI. What we’ve found is that it’s not good for creation. It’s more a supplemental tool for research. The biggest insult I can give anyone when I get a draft of a presentation or written material is: this feels or looks like it was produced by AI. Our view is that AI is all chip, no salsa. And what people want is salsa. But in terms of content strategy, AI is for research, refining, finding data. Pretty much all of our content starts between someone’s ears.

Do your sons have any interest in doing what you do?

They’re different. The only thing I would recommend to anyone who has kids is to have two, because the most fascinating thing is how different they are. One, if I take a picture, will say to me right away, “No social.” He doesn’t want to be on social media. The other wants to start a podcast with me so he can be famous. They’re just so different, and that’s the fascinating thing. Whenever I meet people who have one kid, I say: just have a second, because you’re going to be fascinated at how different they are.

The thing I find interesting and sort of weird about young people is they’d rather be famous than rich. When I was their age, I absolutely would have chosen money over fame. I do worry a little. I get a lot of negative feedback on some of my content. Some of it’s a function of me saying something stupid or being plain wrong. But a lot of it I also think is just that the bigger footprint you have, the more algorithms enjoy an incendiary comment about you. I worry sometimes about my kids reading that stuff and being upset or thinking less of me.

What does a good week look like for you across all of this?

I’m finally in a position in my life, rounding third, where I really enjoy what I do and the people I work with. Most people don’t get to do something they really enjoy and make good money at. It’s taken me a long time to get there. Consulting and analytics were rewarding, but that was real work. This is fun. I’m not an interesting person. I work, I work out, and I spend time with my boys. That’s about it. My best week is when I get to produce good work, I get to hang out with my boys, eat well and exercise so I don’t become depressed and angry at everybody.

On the day of the 20th anniversary re-release of her book Mating in Captivity, a cultural touchstone on the topic of desire, we’re sharing a conversation between Esther and , Substack’s head of new media, recorded at Temple Bar in SoHo, New York. In this second episode of Open Tab, Esther discusses how she hires and has built her businesses, how work has replaced religion as a source of meaning, whether AI can give good therapy, and how she’s made it her life’s work to re-create the proverbial village online.

Hanne: You talk a lot in your work about security and desire and the balance between them—in families, in work, in all kinds of relationships. What is the relationship between work and risk?

Esther: There are so many ways to answer this. I have never worked for anyone. I’ve worked for clinics, I’ve worked in hospitals, but I’ve never been a full-time employee somewhere. And I always said, I can tolerate the lack of security better than I can tolerate the lack of freedom. This was the life of the therapist. You do it all by yourself. And that’s part of why at some point I feel like I want more, I want something else. I want to meet people. I want a meeting. I’ve never had a meeting. Everybody else complains about boring meetings. I want a meeting with five people who are all thinking out loud together.

The theory on trust and risk has never been conclusive. Do you need to take risks in order to learn to trust, or do you need to trust in order to be able to take risks? That is the big question, and there is no answer to it.

Hanne: Why was the podcast [Where Should We Begin?] not a risk?

Esther: Because I think I know what I’m doing when I meet a couple. Because couples therapy is among the most compelling stories you can hear. Because I know that people are really lonely and have no idea what’s happening in the couple next door, and their best friends can come and tell them they’re divorcing, and they never saw it coming.

Hanne: Many people who are in the act of culture-making notice a moment that musicians call flow. What is that for you?

Esther: I can be in flow in many different situations. As a child of Holocaust survivors who spent years in concentration camps and could not do anything—on some level, in a symbolic way, not being helpless, having agency, being able to have a mark on society or on other people’s lives, having impact, control, change, whichever way you want—that is probably one of the most existentially important things for me. I don’t think of it as risk. I think of it as meaning. I get flow from that. It’s when I feel powerful. I don’t feel helpless. I don’t feel impotent. It’s not a concrete thing. I’ve never really said any of this, actually. It is probably at the core of what drives me. I like to matter, because if I matter, I can’t be erased.

Hanne: You said earlier that you never wanted to build a media business, but you have. What makes you different as a leader?

Esther: Because I’ve always been self-employed, I have gravitated towards people who are like that too: experts in their own field. When they tell me what to do, I listen and I do it, because I think they understand this like I understand that. It’s not really hierarchical. My team tells me what they think, what to do. They speak back. They understand what I know, but they understand what they know, and I think that’s a very different structure.

I expect people to really communicate with each other a lot, because everybody is interdependent with the others. The Substack people need to interact with the podcast people, need to interact with the content people, need to interact with the newsletter, with social. Substack has become that gathering place. That’s why I joined Substack. I needed one place where all these people who were talking to each other could actually put everything together. I always talk about how I wanted to bring the therapeutic ideas into the public square. Now I wanted to create a public square for myself.

Hanne: You are now a very well-known set of ideas and culture in and of yourself. What is it like to be a human and also be a brand?

Esther: I connect to the fact that if people stop me on the street, they don’t just recognize me. They come to tell me they read this, and they listened to that. I was there for their divorce, I was there for their grief, I was there for their heartbreak. People recognize me by my voice. They don’t necessarily know what I look like, but they hear me. I’m on a plane and somebody says, are you who I think you are? I say yes. And then I say, What do you do? Do you read? Do you watch or do you listen? And then depending on whichever way they learn, I say, and what was it? What’s one thing that has actually been useful for you? And then I can handle it. Then I feel like there is substance here.

FOOTNOTES

1. Temple Bar, 332 Hudson St., New York—SoHo fixture with a long bar and low lighting.

2. Summerhill—The progressive boarding school in Suffolk, England, cited by Esther, founded in 1921, where children set their own rules and class attendance is optional.

3. “In Search of Erotic Intelligence”—The article Esther wrote for a professional therapy magazine in response to the Clinton–Lewinsky scandal, which landed on the cover of the Utne Reader and led to her book deal.

4. Mating in Captivity—Translated into more than 30 languages. The bestseller challenged the conventional wisdom that love and desire are natural companions, instead arguing that the qualities that nurture love—security, closeness, predictability—can erode desire. The new edition includes a preface on two decades of cultural change, from dating apps to AI.

5. “The secret to desire in a long-term relationship”—Esther’s viral TED Talk, delivered in a salon rather than on the main stage, improvised from memory.

6. Where Should We Begin?—Esther’s long-running podcast, in which she talks to real life couples and individuals navigating complex relationship issues, for all to listen in.

Emily has worked in media and tech but built her current audience of over 10,000 paid subscribers natively on Substack, post by post. She told us she sees Feed Me as a studio, with extensions like a podcast, job board, and thriving subscriber comments section where she’s “never scared that anything bad is happening.”

Substack co-founder Hamish McKenzie sat down with Emily at Old Town Bar in Manhattan’s Flatiron district to talk about building her independent media business from scratch and the glimmers of hope she sees for media on Substack and beyond.

Location: Old Town Bar, Flatiron, NYC. Order: 1 Guinness each

Conversation Excerpts

Hamish: A lot of Feed Me is about money, power, and status. How does that influence how you do [your] job?

Emily: Well, I’ve had a lot of jobs, which has opened me up to a lot of different networks of people. So I’m not coming out of journalism school and writing about the DTC world, or about the hospitality world, or about newsrooms that I’ve never been in. I’ve worked in newsrooms, I’ve worked in venture-backed companies, I’ve worked at Facebook, so I can write about all these things—I don’t want to say “with authority”—but with experience. I know what the chairs feel like in the Meta offices at Hudson Yards.

Hamish: What do they feel like?

Emily: Bouncy, like very adjustable. Everything is like, bring it up, bring it down. I know what the New York Magazine office—

Hamish: What are those chairs like compared to Facebook’s?

Emily: That was the only job that I had a proper cubicle at. It was at the old Varick Street office when Adam Moss was the editor. I loved that job so much. Olivia Nuzzi was one of the first women to ever come up to my desk and be like, do you want to go smoke a cigarette? That happened to me. I’m not writing about her from over here. I hung out with her. You build up your own sources. You’re not blind-calling anyone, because you’ve been around a bit. I think that has given me a lot of perspective when I write about work.

A big thing when I started Feed Me in its current form is that I like to write about the way that people spend money and what that says about them. And I think that’s changed a bit. It’s a little bit more like New York news, and it’s probably a little bit less judgy about how people literally spend money. I think I was probably forcing myself into that narrative a bit.

Hamish: You used to be more judgy?

Emily: I didn’t have an audience. I could hit so hard. I have so many people watching me now, it’s hard. I also don’t really have a team, so if I have a bad day, there’s nobody I’m really looking at [who’s] being like, “It’s fine.”

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Emily: I worked at Meta, and during Covid I started writing on Substack. I started writing short horror fiction that was super informed by my time working in social media and the sort of consumer moment that was happening. Matt Levine from Bloomberg linked to one of those stories in his newsletter, and a bunch of my friends sent me photos of their terminals. They were like, “Levine put you in Money Stuff.” And I was like, wait, you’re reading newsletters for pleasure, and there’s cross-promotion in newsletters? It opened my eyes to the traffic potential but also the pleasure potential of reading newsletters. Because in the past, it was like this chore that you gave to somebody on the audience team, like “Aggregate a bunch of stuff and put it in the newsletter.” It has to happen, nobody wants to do it, but we have to send it.

Hamish: The newsletters were used to try and drive traffic to the stories of the property.

Emily: Right, right. To check off a box. And the best-case scenario was that somebody wouldn’t [flag] it [as] spam or unsubscribe. And I was freelance writing at the time while I was at Meta. I wrote this story about the phenomenon of “shoppy shops” for New York Magazine. I thought: tech people want more of this. Consumers want more of this kind of writing. And the CPG brands and marketers also want to be talking about this more. So I started writing shorter versions of that every day behind a paywall on Substack.

Hamish: Why did you do the paywall?

Emily: Because I could, and I wanted a little bit of space. I didn’t have an online following. So I was just like, let me keep this safe and protected, and if you really want to read it, you can. I had really hot takes, and at the time most of my friends who were having those kinds of takes were being taken care of by an editor, to make their takes cooler or safer or maybe a bit more palatable.

Hamish: People appreciated that you didn’t have that filter. And you put it behind a paywall, so it’s kind of like a secret club.

Emily: Exactly. And I think that’s why my comment section... I mean, there are thousands and thousands of paid readers below that paywall now. It’s such a wonderful experience. Every day when I see my comment section, I’m never scared that anything bad is happening there.

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Hamish: So what does it feel like to be the owner of this business and responsible for this thing that is suddenly big?

Emily: It’s great. It’s a big business. You guys see the network effects of it all, and how many people read it. Everyone sees how big it is because of the leaderboards, which is great for me. I’m very proud that I have amassed that many people without, you know, bringing them over from somewhere else. But that part of the job is also pressure, like the purple checkmark. It doesn’t not put a target on your back as a journalist, because it’s so different from other people who are working in journalism who are not having the same type of experience at all.

Hamish: The purple checkmark on Substack means you’ve got at least 10,000 paying subscribers. And so a lot of journalists are probably looking at their shrinking newsrooms, the jobs disappearing, the insecurity... and potentially jealous of that, do you think?

Emily: Yeah. People can do back-of-napkin math and figure out how much money I’m making, and I’m sort of tired of being on panels and always being asked that. And then being followed on a talk or panel by an investor or a CEO of a media company who’s never asked that. That’s something I started actually pushing back on in interviews.

Hamish: Do you think that’s because you’re a young woman running the business, or do you think it’s a media business curiosity thing?

Emily: I think it’s both. But a smart person can also see that I’m putting money back into my writers and I’m putting money back into my free parties. I also know that I’m doing more than just writing. I’m a product manager, a social media manager, a graphic designer. I’m emailing my warehouse all the time, talking on the phone with them about stocking products. I’m running payroll. I’m an event planner, an event producer. I do a lot of jobs. And I love my job. I feel crazy half the time, which might be coming through in this conversation, but it’s an awesome job. I feel really grateful when I can connect with other media operators and trust them and get along with them. But I also feel like there’s this competitiveness, especially with people who have been doing this longer than me and might look at me like, where the fuck did you come from?

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Emily: What’s cool is that a lot of the people that write for me aren’t career writers. , who hosts Expense Account, the Feed Me podcast about restaurants—he’s an artist, he was a wine distributor. He’s not a writer by background; he’s just an excellent writer. And Teddy, who writes about movies and entertainment—he asked if he could go to Sundance. And I was like, I kind of want to go to Sundance, but I’m not going to go because I have this SF trip. And I was like, yeah, put together a budget, tell me what it would look like. Yeah, go. We can run this. Nobody else is writing about it. Get in there. Be weird. I love identifying interesting people and then doubling down on them and having them build out their own little worlds within the newsletter. But it’s also real—I’ve never managed anybody before, so it’s new for me and I’m learning as I’m doing it. The only thing I can do is talk to other media operators who have been through it and try to get best practices from them. There are some true business benefits to running a newsletter on Substack—and this isn’t an ad—but a lot of the operations are sort of dealt with, and the founders and the other people that work at the company are so present on the feed that you can reach out to them and get a response.

Hamish: I hear they’re real pricks.

Emily: No, they’re great. They’re really great and they’re very interesting. There’s this backend foundation, and that is why you guys take a cut of writers’ income, but that has never been a problem to me.

Hamish: Well, to try and broaden it: we’ve always tried to take all the bullshit off the table for our writers so they can focus on the most important thing, which is the work itself, the editorial work. How do you feel about where the media ecosystem is going, what media jobs or the future might look like? People are feeling a lot of doom and gloom at the moment, but do you have any feelings of optimism?

Emily: Here’s what I’m wary of: taking cash up front for a business that doesn’t exist yet. I think raising money is risky. As somebody who’s never done it and runs a really successful media business, venture capital in general scares me. But I’ve seen glimmers of hope in a few different places. I think food media is one of them. I think we’ll see some of these people come out and win. I wouldn’t be surprised if by the end of the year Puck launched a food vertical. I wouldn’t be surprised if Punchbowl, the D.C.-based publication, launched more lifestyle stuff. I think people want more niche, specific news that they’re interested in. I’m also seeing a lot of local news publications on Substack that make me really happy. I don’t know if these people are doing it for the love of the game or to try to make a lot of money, but there’s the , which is just for Boerum Hill, and the East Side Rag, which is focused on Silver Lake and Echo Park. They’re making people really happy and feel connected to their neighborhoods in a way that newspapers used to do. I don’t think that everybody is in this game to make a ton of money and then sell and buy a house in the Hamptons. I think some people are truly just trying to better their community and spread information and make interesting content.

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Emily: I almost feel better about my job when I talk to friends who work in totally different industries. I learned some of my best qualities as a good person and a good operator from people who don’t do anything close to this. Like talking to my friends who are moms who just get their kids to school on time, or make sure to send a birthday card... just good people. And that sort of radiates out. Show up to things. Bring somebody a birthday present. Respond to the text. Do things that you say you’ll do. Life is easier after that because you know where you stand.

Footnotes

Rabbit holes and references from the show

1. Old Town Bar, 45 E. 18th St., New York. Longtime media drinking hole in operation since 1901, making it one of the oldest bars in New York City. Novelist Pete Hamill, a longtime teetotaler, reportedly said of it: “If I ever had a drink again, this would be the place.”

2. The Bloomberg burger

   

3. Great Jones—The DTC cookware startup where Emily worked.

4. Emily in Matt Levine’s Money Stuff—The Bloomberg newsletter that linked to Emily’s early Substack fiction.

5. Long Island, NY

6. NY Mag’s Welcome to the Shoppy Shop.

7. Newsday’s Kidsday—Early scoops from the early aughts.

   

8. Feed Me merch in the wild

   

9. The End—Emily’s short documentary about Gardiner’s Island, the oldest privately owned island in America.

10. —Hyperlocal Substack covering Boerum Hill, Brooklyn.

11. East Side Rag—Substack focused on Silver Lake and Echo Park in Los Angeles.

12. The Machine in the Garden

13. ’s Fashion Week reporting

14. Nothing sexy happens on Slack—Emily’s survey on sex and the workplace.

    Feed Me

    "Nothing sexy happens on Slack."

    Yesterday, I wrote about a study that said 50% of people currently have a work crush. All around the office, managers, direct reports, CEOs and peers are spending some untold portion of company time daydreaming about or flirting with each other. When I posted about this on my Instagram Story, a flood of DMs from strangers started sharing their office romance stories with me, so I decided to run an anonymous survey about how and why people engage in something so risky, and got hundreds of remarkably vulnerable, albeit anonymous, responses…

    Read more

    2 years ago · 70 likes · 27 comments · Emily Sundberg

15. And lastly, Babygirl—The Nicole Kidman office-sex drama that Emily says inspired the survey.

Substack for Media Founders

New episodes of Open Tab drop weekly through June. You can watch on YouTube, listen wherever you get your podcasts, and always find the full series here on Substack.